Sodium borohydride → HCID 178476301、化合物

HRID 1486217

反応式

HRID 1486217 の反応式
C(O)CO.C(=O)=O.[C:8]([O:11][CH2:12][CH2:13][C@H:14]1[CH2:19][CH2:18][C@H:17]([CH:20]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH:22]=[O:23])[CH2:16][CH2:15]1)(=[O:10])[CH3:9].[BH4-].[Na+]>C(O)C>[C:8]([O:11][CH2:12][CH2:13][C@H:14]1[CH2:19][CH2:18][C@H:17]([CH:20]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:22][OH:23])[CH2:16][CH2:15]1)(=[O:10])[CH3:9]

参加物

5

反応物 3

HCID 4311764Sodium borohydrideHCID 86601574Dry ice ethyleneglycolHCID 178476300HCID 178476300、化合物

生成物 1

HCID 178476301HCID 178476301、化合物収率 53%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
0 °C

実験手順

To a cooled (ethylene glycol+dry ice) solution of 2-(trans-4-(1-(tert-butoxycarbonylamino)-3-oxopropyl)cyclohexyl)ethyl acetate (1.88 g, 5.5 mmol) in ethanol (90 mL) was added NaBH4 (0.212 g, 5.5 mmol). The mixture was stirred at −10˜15° C. for 10 min and 0° C. for 10 min, and then quenched by addition of saturated aqueous NH4Cl solution (30 mL) and brine (30 mL). After removal of the volatile by evaporation, the aqueous residue was extracted with EtOAc, dried over Na2SO4. Purification by flash column chromatography (eluent: 30% EtOAc in hexanes to 40%) gave the alcohol product (1.0 g, 53%). LC/MC: 366.1 (MNa)+.

後処理

  1. customquenched by addition of saturated aqueous NH4Cl solution (30 mL) and brine (30 mL)
  2. customAfter removal of the
  3. customvolatile by evaporation
  4. extractionthe aqueous residue was extracted with EtOAc
  5. dry with materialdried over Na2SO4
  6. customPurification by flash column chromatography (eluent: 30% EtOAc in hexanes to 40%)

出典と根拠

ORDレコード
ord-a1d9572169cb42218c691f0f2f162e02
出典データセット
uspto-grants-2016_08
特許番号
US09422314B2

関連ノート

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