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

HRID 30069

Reaction equation

HRID 30069 reaction equation
[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[CH2:17][C:16](=[O:18])[CH2:15][CH2:14][CH:13]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])[CH2:3][CH2:2]1.CO.[BH4-].[Na+]>COCCOC>[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[CH2:17][CH:16]([OH:18])[CH2:15][CH2:14][CH:13]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

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 68985626(+/-)-3,4-Bis-cyclopropylmethoxy-N-[(1RS,2RS)-2-(3,4-dimethoxyphenyl)-5-oxo-cyclohexyl]-benzamide2×

Product 1

HCID 68986614(+/-)-3,4-bis-cyclopropylmethoxy-N-[(1RS,2RS,5RS)-2-(3,4-dimethoxyphenyl)-5-hydroxycyclohexyl]benzamideYield 87.8%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

7.2 g of (±)-3,4-bis-cyclopropylmethoxy-N-[(1RS,2RS)-2-(3,4-dimethoxyphenyl)-5-oxo-cyclohexyl]benzamide (compound C1) are dissolved in 550 ml of 1,2-dimethoxyethane and 34 ml of methanol and treated portionwise with 600 mg of sodium borohydride at room temperature. The reaction mixture is concentrated, the residue redissolved in ethyl acetate and extracted with water. The organic layer is dried using sodium sulfate, concentrated and the residue is chromatographed on silica gel using a mixture of petroleum ether/ethyl acetate/triethylamine in the ratio 6/3/1. 6.35 g of the title compound are obtained.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. dissolutionthe residue redissolved in ethyl acetate
  3. extractionextracted with water
  4. customThe organic layer is dried
  5. concentrationconcentrated
  6. customthe residue is chromatographed on silica gel using
  7. additiona mixture of petroleum ether/ethyl acetate/triethylamine in the ratio 6/3/1

Sources & evidence

ORD record
ord-139f86a240e746ed8d655d833f32d368
Source dataset
uspto-grants-2008_09
Patent number
US07423046B2

Linked notes

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