Ammonium Acetate → HCID 67072976, compound

HRID 1948172Notes

Reaction equation

HRID 1948172 reaction equation
[CH2:1]([O:8][C:9](=[O:22])[NH:10][CH:11]([C:14]1([CH3:21])[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:29].[Na+]>CO>[CH2:1]([O:8][C:9](=[O:22])[NH:10][CH:11]([C:14]1([CH3:21])[CH2:19][CH2:18][CH:17]([NH2:29])[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 70236756HCID 70236756, compound

Product 1

HCID 67072976HCID 67072976, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.10 g (6.92 mmol) of the ketone (78) were dissolved in 21 mL of absolute methanol, then 5.34 g (69.2 mmol) of ammonium acetate and 435 mg (6.92 mmol) of sodium cyanoborohydride were added, and the mixture was stirred at room temperature for 16 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 1.70 g of the title compound 79 in a purity sufficient to be used directly in the next step. Rt=0.75 min (Method P). Detected mass: 305.2 (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-657870442bba457fa7dfaadb1bd81a1d
Source dataset
uspto-grants-2013_03
Patent number
US08399482B2

Reaction notes

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