Ammonium Acetate → {1-[4-Amino-1-(4-methoxy-phenyl)-cyclohexyl]-propyl}carbamic acid benzyl ester

HRID 45196

Reaction equation

HRID 45196 reaction equation
[CH2:1]([O:8][C:9](=[O:29])[NH:10][CH:11]([C:14]1([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]1)[CH2:12][CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:36].[Na+]>CO>[CH2:1]([O:8][C:9](=[O:29])[NH:10][CH:11]([C:14]1([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[CH2:19][CH2:18][CH:17]([NH2:36])[CH2:16][CH2:15]1)[CH2:12][CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 58380957{1-[1-(4-Methoxy-phenyl)-4-oxo-cyclohexyl]-propyl}-carbamic acid benzyl ester

Product 1

HCID 58380970{1-[4-Amino-1-(4-methoxy-phenyl)-cyclohexyl]-propyl}carbamic acid benzyl esterYield 74.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

200 mg (0.51 mmol) of the ketone (97) were dissolved in 1.5 mL of absolute methanol, then 390 mg (5.06 mmol) of ammonium acetate and 31.8 mg (0.51 mmol) of sodium cyanoborohydride were added, and the mixture was stirred at room temperature for 2 h. The reaction mixture was evaporated, the residue dissolved in 50 mL of 1N aqueous sodium hydroxide and extracted twice with 100 mL of dichloromethane. The combined organic layer was dried over magnesium sulphate, filtered, and evaporated to give 150 mg of the title compound 98 in a purity sufficient to be used directly in the next step. Rt=1.18 min (Method 19). Detected mass: 397.3 (M+H+).

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutionthe residue dissolved in 50 mL of 1N aqueous sodium hydroxide
  3. extractionextracted twice with 100 mL of dichloromethane
  4. dry with materialThe combined organic layer was dried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-5ea78663d3ae494da452edd7ff86087b
Source dataset
uspto-grants-2013_09
Patent number
US08541449B2

Linked notes

Loading…