Asymmetric synthesis of (+)-CP-99,994 and (+)-L-733,060 from enantiomerically pure (3S,4S)-4-(tert-butylcarbamoyl)-4-phenyl-1-buten-3-ol

Synlett

Volumn , Issue 20, 2006, Pages 3395-3398

  Oshitari, Tetsuta ^a   Mandai, Tadakatsu ^a  

^a KURASHIKI UNIVERSITY OF SCIENCE AND THE ARTS   (Japan)

Author keywords

1,2 Amino alcohols; 1,2 Diamines; Hydroformylations; Neurokinin 1 antagonists; Piperidines

Indexed keywords

3 (2 METHOXYBENZYLAMINO) 2 PHENYLPIPERIDINE; 3 [3,5 BIS(TRIFLUOROMETHYL)BENZYLOXY] 2 PHENYLPIPERIDINE; 4 (TERT BUTYLCARBAMOYL) 4 PHENYL 1 BUTEN 3 OL; BENZENE DERIVATIVE; SUBSTANCE P ANTAGONIST; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; DRUG SYNTHESIS; ENANTIOMER;

EID: 33846551224     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-956453     Document Type: Article

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46. 3.
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60. Five-membered N-Boc-enamide (2%) and five-membered N-Boc-aminals (5%) were also isolated after the treatment with CSA. N-Ts-enamide and N-Ts-aminals were not obtained at all.
61. 4S: C, 64.46; H, 6.59; N, 6.54. Found: C, 64.37; H, 6.71; N, 6.54.
62. In the absence of TBAI, the N-alkylation was very slow at 0 °C. Compound 12, however, was afforded in 81% yield at r.t. in 5 h with the significant loss of enantiomeric purity (77% ee), which was probably caused by the elimination-addition sequence of the N-2-methoxybenzyl-tert- butyl carbamoyl group.
63. R(ent-12) = 11.0 min].
64. 3): δ = 20.4, 28.2, 46.7, 47.8, 54.7, 54.8, 64.0, 109.8, 120.0, 126.3, 126.5, 127.8, 128.2, 129.6, 142.4, 157.6.
65. Protection of C3-hydroxyl group as a benzoate was of choice for the subsequent hydroformylation.
66. 4: C, 72.80; H, 6.64; N, 3.69. Found: C, 72.76; H, 6.84; N, 3.66.
67. Five-membered aminals (4%) were also isolated.
68. R(ent-14) = 5.75 min].
69. R(ent-15) = 16.6 min)].
70. 3): δ = 20.5, 28.4, 47.1, 64.2, 70.0, 77.3, 121.1 (hept, J = 4.1 Hz), 123.2 (q, J = 271 Hz), 126.7, 127.0, 127.4 (m), 128.1, 131.2 (q, J = 32.9 Hz), 141.2, 141.9.