Sodium hydride → (4aR*,8aR*)-2-oxo-octahydro-pyrido[3,4-b][1,4]oxazine-6-carboxylic acid tert-butyl ester

HRID 2066542노트

반응식

HRID 2066542 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@@H:11]([NH:14][C:15](=[O:18])[CH2:16]Cl)[C@H:10]([OH:19])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@@H:11]2[C@H:10]([O:19][CH2:16][C:15](=[O:18])[NH:14]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 24758Sodium hydrideHCID 58745622(3R*,4R*)-4-(2-chloro-acetylamino)-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 58745484(4aR*,8aR*)-2-oxo-octahydro-pyrido[3,4-b][1,4]oxazine-6-carboxylic acid tert-butyl ester수율 55.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirring solution of (3R*,4R*)-4-(2-chloro-acetylamino)-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (2.70 g, 9.23 mmol) in tetrahydrofuran (30 mL) cooled down to 0° C. was added sodium hydride, 60% dispersion in mineral oil (830 mg, 1.1 eq) portionwise. The mixture was warmed to room temperature and stirred for 6 hours. The mixture was partitioned between dichloromethane and brine. The combined organic layers were washed with brine, separated and dried (MgSO4). The crude product was purified by column chromatography to yield (4aR*,8aR*)-2-oxo-octahydro-pyrido[3,4-b][1,4]oxazine-6-carboxylic acid tert-butyl ester (1.31 g).

후처리

  1. customThe mixture was partitioned between dichloromethane and brine
  2. washThe combined organic layers were washed with brine
  3. customseparated
  4. dry with materialdried (MgSO4)
  5. customThe crude product was purified by column chromatography

출처 및 근거

ORD 기록
ord-82c11d40ea6c4ab69a01843698f665a5
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08293735B2

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