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

HRID 2066542ノート

反応式

HRID 2066542 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-82c11d40ea6c4ab69a01843698f665a5
出典データセット
uspto-grants-2012_10
特許番号
US08293735B2

反応ノート

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