(2S)-2-(2,3,4-Trifluoroanilino)propanol → (3S)-3-Methyl-7,8-difluoro-2,3-dihydro-4H-1,4-benzoxazine

HRID 8482노트

반응식

HRID 8482 반응식
CC(C)([O-])C.[K+].F[C:8]1[C:18]([F:19])=[C:17]([F:20])[CH:16]=[CH:15][C:9]=1[NH:10][C@@H:11]([CH3:14])[CH2:12][OH:13]>CN(C=O)C>[F:20][C:17]1[CH:16]=[CH:15][C:9]2[NH:10][C@@H:11]([CH3:14])[CH2:12][O:13][C:8]=2[C:18]=1[F:19]

참가 물질

4

반응물 2

HCID 11401466(2S)-2-(2,3,4-Trifluoroanilino)propanolHCID 23665647Potassium tert-butoxide

생성물 1

HCID 11041424(3S)-3-Methyl-7,8-difluoro-2,3-dihydro-4H-1,4-benzoxazine수율 79.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To DMF (2 ml) was added potassium tertiary-butoxide (110 mg) under ice-cooling. Next, a solution of the compound (100 mg) obtained in Example 51 in DMF was dropped thereinto and the obtained mixture was stirred for 30 minutes. After treating in a conventional manner, the mixture was subjected to silica gel column chromatography to give 72 mg (79%) of the title compound. The optical purity determined by HPCL was >94% ee. Various spectral data was identical with those of a specimen synthesized separately.

후처리

  1. temperaturecooling
  2. additionAfter treating in a conventional manner

출처 및 근거

ORD 기록
ord-660669f44f7a4e25a072a55d2b7faf91
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087778B2

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