Methanol → (+/-)-3,4-bis-cyclopropylmethoxy-N-[(1RS,2RS,5RS)-2-(3,4-dimethoxyphenyl)-5-hydroxycyclohexyl]benzamide

HRID 30071노트

반응식

HRID 30071 반응식
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH:29]=[CH:30][C:31]=2[O:32][CH2:33][CH:34]2[CH2:36][CH2:35]2)[C:9]([NH:11][CH:12]2[CH:18]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=3)[CH2:17][CH:16]3[CH:14]([O:15]3)[CH2:13]2)=[O:10])[CH2:3][CH2:2]1.[BH4-].[Na+].CO.O>C(O)(C)(C)C.C(OCC)(=O)C>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH:29]=[CH:30][C:31]=2[O:32][CH2:33][CH:34]2[CH2:35][CH2:36]2)[C:9]([NH:11][CH:12]2[CH2:13][CH:14]([OH:15])[CH2:16][CH2:17][CH:18]2[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=2)=[O:10])[CH2:2][CH2:3]1

참가 물질

7

반응물 4

HCID 887MethanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 86601279(+/-)-3,4-bis-cyclopropylmethoxy-N-[(3RS,4RS)-4-(3,4-dimethoxyphenyl)-7-oxabicyclo[4.1.0]-hept-3-yl]benzamide2회

생성물 1

HCID 68986614(+/-)-3,4-bis-cyclopropylmethoxy-N-[(1RS,2RS,5RS)-2-(3,4-dimethoxyphenyl)-5-hydroxycyclohexyl]benzamide수율 68.2%

시약·촉매·용매 2

HCID 6386tert-Butanol용매HCID 8857Ethyl Acetate용매

실험 절차

16.5 g of (±)-3,4-bis-cyclopropylmethoxy-N-[(3RS,4RS)-4-(3,4-dimethoxyphenyl)-7-oxabicyclo[4.1.0]-hept-3-yl]benzamide (compound E1) are dissolved in 500 ml of tert-butanol, 5.0 g of sodium borohydride are added and the reaction mixture is heated to boiling. After slow addition of 70 ml of methanol, the reaction mixture is cooled and treated with 200 ml of water and 150 ml of ethyl acetate. The organic phase is dried using sodium sulfate, concentrated and the residue is chromatographed on silica gel using a mixture of petroleum ether/ethyl acetate in the ratio 1/2. 11.3 g of the title compound are obtained.

후처리

  1. temperaturethe reaction mixture is heated to boiling
  2. temperaturethe reaction mixture is cooled
  3. customThe organic phase is dried
  4. concentrationconcentrated
  5. customthe residue is chromatographed on silica gel using
  6. additiona mixture of petroleum ether/ethyl acetate in the ratio 1/2

출처 및 근거

ORD 기록
ord-887b89fa857b4adb9f116c835ffbcbb4
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423046B2

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