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Volumn , Issue 12, 2009, Pages 1923-1928

Synthesis of β-amino alcohols via the reduction of lactamides derived from ethyl (2S)-lactate with borane-methyl sulfide

Author keywords

Amino alcohols; Asymmetric synthesis; Borane methyl sulfide; Lactamides; Reductions

Indexed keywords

AMIDE; AMINOALCOHOL; BORANE DERIVATIVE; BORON TRIFLUORIDE; DIMETHYL SULFIDE; LACTIC ACID ETHYL ESTER;

EID: 67749091047     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1217538     Document Type: Article
Times cited : (10)

References (90)
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    • Cost per gram from Aldrich Chemical Company: ethyl (2S)-lactate: £0.05; (2S)-2-methyloxirane: £8.66.
    • Cost per gram from Aldrich Chemical Company: ethyl (2S)-lactate: £0.05; (2S)-2-methyloxirane: £8.66.
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    • 4: (a) See ref. 13d.
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    • 4: (d) Taoka, N, Yasohara, Y, Yao, T, Maehara, K, Ueda, Y. WO 2002070482, 2002
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    • Synthesis of Lactamides 8a-n, General Procedure Ethyl (2S)-lactate (7, 88.2 mmol, 1 equiv) and the appropriate amine (114.6 mmol, 1.3 equiv) were placed in a flask and heated under reflux for 24 h. The solution was allowed to cool to r.t, the volatiles were removed under reduced pressure (1.33·10-4 bar, and the lactamide was purified by vacuum distillation or recrystallization. For the synthesis of bislactamides 8k and 8l, 0.5 equiv of amine were used. Compounds 8a-d,f-j,l-n are known.20 Characterization Data for 8e Yellow oil, bp 101-104°C (1.33·10-4 bar, α] D16 -16.6 (c 1.31, CHCl3, IR (neat, 3308 (OH, NH, 2978, 1655 (C=O, 1532, 1457, 1364, 1275, 1124, 1048, 978 cm -1. 1H NMR (400.1 MHz, CDCl3, δ, 6.90 (s, 1 H, exch. D2O, NH, 4.18 (q, J, 6.5 Hz, 1 H, CHOH, 3.84 b
    • +: 227.1008; found: 227.1010.
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    • 67749146553 scopus 로고    scopus 로고
    • Synthesis of β-Amino Alcohols 9a-n, General Procedure The lactamide 8 (23.7 mmol, 1 equiv) was dissolved in dry 1,2-dimethoxyethane (15 mL/g) in an oven-dried flask equipped with a Dean-Stark trap and reflux condenser under a nitrogen atmosphere. Boron trifluoride etherate (47.5 mmol, 2 equiv) was added, and then borane-methyl sulfide (47.5 mmol, 2 equiv) was added dropwise via syringe. Once the evolution of H2 had ceased, the solution was heated under reflux for 24 h (ca. 2-3 mL of distillate collected) and the solvents were removed in vacuo. The resulting colorless oil was carefully diluted with 6 M HCl (15 mL/g) and boiled for ca. 5 min. The resulting clear solution was neutralized while still hot with 6 M NaOH (15 mL/g) and then allowed to cool to r.t. before being saturated with solid K2CO3 and extracted with CHCl3 3 x 50 mL, The combined organic extracts were dried over MgSO4 and evaporated to afford the crude β-amino al
    • 2)
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    • Lactamides 8a-d have recently been used as chiral auxiliaries, see: Ammazzalorso, A.; Amoroso, R.; Bettoni, G.; De Filippis, B.; Fantacuzzi, M.; Giampietro, L.; Maccallini, C.; Tricca, M. L. Eur. J. Org. Chem. 2006, 4088.
    • Lactamides 8a-d have recently been used as chiral auxiliaries, see: Ammazzalorso, A.; Amoroso, R.; Bettoni, G.; De Filippis, B.; Fantacuzzi, M.; Giampietro, L.; Maccallini, C.; Tricca, M. L. Eur. J. Org. Chem. 2006, 4088.
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    • Compound 8a: (a) See ref. 13a.
    • Compound 8a: (a) See ref. 13a.
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    • See ref. 13a
    • (d) See ref. 13a.
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    • See ref. 20c
    • (f) See ref. 20c.
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    • Compound 8c: (g) See ref. 13a.
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    • Compound 8d: (j) See ref. 19.
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    • Racemic 8f: (k) See ref 13a,c
    • Racemic 8f: (k) See ref 13a,c.
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    • Compound 8n: (t) See ref. 20s.
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    • Racemic 9a: (a) Reid, W. B.; Wright, J. B. Jr.; Kolloff, H. G.; Hunter, J. H. J. Am. Chem. Soc. 1948, 70, 3100.
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    • Compound 9h: (j) Kashima, C.; Harada, K. J. Chem. Soc., Perkin Trans. 1 1988, 1521.
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    • Compound 9i: (m) See ref. 14b.
    • Compound 9i: (m) See ref. 14b.
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    • See ref. 14c
    • (n) See ref. 14c.
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    • Compound 9j: (o) See ref. 14b.
    • Compound 9j: (o) See ref. 14b.
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    • See ref. 14c
    • (p) See ref. 14c.
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    • Racemic 9k: (q) Steck, E. A.; Buck, J. S.; Fletcher, L. T. J. Am. Chem. Soc. 1957, 79, 4414.
    • Racemic 9k: (q) Steck, E. A.; Buck, J. S.; Fletcher, L. T. J. Am. Chem. Soc. 1957, 79, 4414.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.