Sodium Carbonate → HCID 178472458, 화합물

HRID 2202719노트

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HRID 2202719 반응식
[CH3:1][CH2:2][O:3][C:4]([CH:6]1[CH2:12][CH2:11][C:9](=O)[CH2:8][CH2:7]1)=[O:5].[C:13]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])(=[O:16])[NH:14][NH2:15].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])([O-])=O.[Na+].[Na+]>ClCCl.CC(O)=O>[CH2:2]([O:3][C:4]([C@H:6]1[CH2:12][CH2:11][C@H:9]([NH:15][NH:14][C:13]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:8][CH2:7]1)=[O:5])[CH3:1]

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 70091tert-Butyl carbazateHCID 317638Ethyl 4-oxocyclohexanecarboxylateHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 178472458HCID 178472458, 화합물

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 4-cyclohexanonecarboxylic acid ethyl ester (5.0 g, 29.0 mmol) and tert-butyl carbazate (3.9 g, 29.4 mmol) in dichlorometane (250 mL) and AcOH (4 mL) was added NaBH(OAc)3 (18.7 g, 88.0 mmol) gradually at 0° C. After addition, the mixture was stirred at the same temperature for 3 h, then allowed to warm to room temperature and stirred for 20 h. The reaction mixture was poured into saturated aqueous Na2CO3 solution and extracted with DCM. The DCM extracts were washed with brine×2 and dried over MgSO4. After the solvent was removed, the residue was purified by column chromatography on silica gel to give compound D1-1 (3.0 g, 36%) as a white solid.

후처리

  1. additionAfter addition
  2. stirringstirred for 20 h
  3. extractionextracted with DCM
  4. washThe DCM extracts were washed with brine×2
  5. dry with materialdried over MgSO4
  6. customAfter the solvent was removed
  7. customthe residue was purified by column chromatography on silica gel
  8. customto give compound D1-1 (3.0 g, 36%) as a white solid

출처 및 근거

ORD 기록
ord-0d7f95553a0249029a363e0698482e25
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365522B2

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