SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 6, 2008, Pages 875-879

First example of s-BuLi/(-)-sparteine-mediated chiral deprotonation of a piperazine and proof of the sense of induction

(3) McDermott, Benjamin P a Campbell, Andrew D a Ertan, Anne b

a ASTRAZENECA (United Kingdom)

b ASTRAZENECA R AND D (Sweden)

Author keywords

( ) sparteine; Asymmetric deprotonation; Lithiation; N tert butylpiperazine synthesis; Piperazines

Indexed keywords

CARBON DIOXIDE; CARBOXYLIC ACID DERIVATIVE; LITHIUM DERIVATIVE; NITROGEN DERIVATIVE; PIPERAZINE; SPARTEINE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CYCLIZATION; ENANTIOMER; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 42049111415 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1042905 Document Type: Article

Times cited : (31)

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21
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- N-(tert-Butyl)piperazine is advertised as a commercially available compound. A sample ordered and received by us was, in fact, identified as N-(n-butyl)piperazine. Another company advertising the compound has now discontinued this product.

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25
- 42049121919
- R)-tert-Butyl 2-(4-Benzylpiperazine- 1-carbonyl)-4-tert-butylpiperazine-1-carboxylate (11) To a solution of tert-butyl 4-tert-butylpiperazine-1-carboxylate (500 mg, 2.1 mmol) and, )-sparteine (0.62 mL, 2.7 mmol) in Et2O (20 mL) at -78°C under argon was added s-BuLi (1.92 mL, 2.7 mmol) dropwise. The resulting Suspension was stirred at -78°C for 5 h and then CO 2 was bubbled through the mixture via syringe for 30 min. After the addition of one pellet of CO2 the reaction was allowed to warm to 0°C and then quenched with H2O (0.5 mL, The mixture was diluted with CH2Cl2 and Na2SO4 was added. The mixture was stirred for 5 min then filtered and concentrated at reduced pressure to give a light yellow oil. To a solution of this material in DMF (15 mL) at r.t. was added benzylpiperazine (0.30 mL, 1.7 mmol, DIPEA 0.58
- R (S) = 6.52 min.

26
- 42049108865
- Selected Analytical Data Compound 1: white solid; mp 89°C; [α]D20 +9.5 (c 1.00, EtOH, 1H NMR (500 MHz, DMSO, 373 K, δ, 1.00 (s, 9 H, 1.38 (s, 9 H, 2.11 (td, J, 11.4, 4.2 Hz, 1 H, 2.38 (dd, J, 12.0,4.8 Hz, 1 H, 2.68-2.76 (m, 4H, 3.08 (dt, J, 12.2, 2.5 Hz, 1 H, 3.33-3.51 (m, 6 H, 3.61 (dt, J= 12.3, 3.1 Hz, 1 H, 4.67-4.70 (m, 1 H, 13C NMR (126 MHz, DMSO, δ, 18.49, 25.58, 27.98, 42.34, 45.01, 45.64, 47.05, 53.00, 55.98, 78.58, 155.11, 169.06. ESI-HRMS: m/z calcd for C25H 41N4O3: 355.27037; found: 355.27036 [M, H, Compound 12: white solid; mp 165°C; [α] D20 +11.0 (c 1.00, EtOH, 1NMR (400 MHz, CDCl3, δ, 1.07 (s, 9 H, 2.01-2.18 (m, 2 H, 2.22 (s, 3 H, 2.83-3.13 (m, 4 H, 3.35-3.89 (m, 10 H, 13C NMR 101 MHz, CDCl 3
- +.

27
- 42049121920
- C30H47N5O6S.C 2H4Cl2, Mr, 704.75, colourless block. Crystal dimensions: 0.20 x 0.15 x 0.03 mm, monoclinic, space group P21 α, 6.0241(3) Å, b, 19.1591(7) Å, c, 15.9244(8) Å, β, 99.631(2)°, V, 1812.03(14) Å3, Z, 2, Dx, 1.292 Mg m-3. Reflections collected: 25197; independent reflections: 8012 (Rint, 0.042, final R[F2 > 2σ (F2, 0.052, R (all data, 0.1249, wR(F2, 0.137. Flack parameter: -0.01 7, Crystallographic data for this structure has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 668196. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road Cambridge, CB2 1EZ, UK [fax
- 2) = 0.137. Flack parameter: -0.01 (7). Crystallographic data for this structure has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 668196. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road Cambridge, CB2 1EZ, UK [fax: +44 (1223)336033; e-mail: deposit@ccdc.cam.ac.uk].

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