Sodium borohydride → HCID 178476301, 화합물

HRID 1486217

반응식

HRID 1486217 반응식
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]

참가 물질

5

반응물 3

HCID 4311764Sodium borohydrideHCID 86601574Dry ice ethyleneglycolHCID 178476300HCID 178476300, 화합물

생성물 1

HCID 178476301HCID 178476301, 화합물수율 53%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
0 °C

실험 절차

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)+.

후처리

  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%)

출처 및 근거

ORD 기록
ord-a1d9572169cb42218c691f0f2f162e02
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09422314B2

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