Ozone → 3-Benzyloxycarbonylamino-3-(2-hydroxy-1-methylethyl)piperidine-1-carboxylic acid tert-butyl ester

HRID 1912391ノート

反応式

HRID 1912391 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([NH:18][C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])([CH:14]([CH3:17])[CH:15]=C)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O:29]=[O+][O-].[BH4-].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([NH:18][C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])([CH:14]([CH3:17])[CH2:15][OH:29])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 24823OzoneHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 582933873-Benzyloxycarbonylamino-3-(1-methylallyl)piperidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 582933703-Benzyloxycarbonylamino-3-(2-hydroxy-1-methylethyl)piperidine-1-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 21584188Chloroform methanol溶媒

実験手順

A solution of an optically-active compound of 3-benzyloxycarbonylamino-3-(1-methylallyl)piperidine-1-carboxylic acid 1-tert-butyl ester (815 mg) in chloroform/methanol (6.6 ml/6.6 ml) cooled to −78° C. was flowed ozone air for 30 minutes. To the reaction mixture was added sodium borohydride (318 mg) in small batches, and then the mixture was warmed to room temperature over 40 minutes. To the mixture was added saturated aqueous sodium bicarbonate solution, and the mixture was extracted with chloroform twice. The combined organic layer was washed with aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=3/2 to 0/1) to give the titled compound (406 mg).

後処理

  1. customfor 30 minutes
  2. extractionthe mixture was extracted with chloroform twice
  3. washThe combined organic layer was washed with aqueous sodium bicarbonate solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=3/2 to 0/1)

出典と根拠

ORDレコード
ord-e048bfe1d4944b3eb3f4b092f1d50a53
出典データセット
uspto-grants-2013_12
特許番号
US08609647B2

反応ノート

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