Ammonium Acetate → HCID 68688308, compound

HRID 2245354Notes

Reaction equation

HRID 2245354 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[C:11](=O)[CH2:10][CH2:9][N:8]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=2)[CH2:7]1)=[O:5])[CH3:2].C([O-])(=O)C.[NH4+].C([BH3-])#[N:29].[Na+]>CO.CCOC(C)=O>[CH2:1]([O:3][C:4]([CH:6]1[CH:11]([NH2:29])[CH2:10][CH2:9][N:8]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=2)[CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 68685507HCID 68685507, compound

Product 1

HCID 68688308HCID 68688308, compoundYield 70.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of rac-1-(3,4-dimethoxy-phenyl)-4-oxo-piperidine-3-carboxylic acid ethyl ester (640 mg) and ammonium acetate (3 g) in 10 ml methanol was stirred 18 h at RT., then sodium cyanoborohydride (2 g) was added. After 18 h at RT, the mixture was diluted with AcOEt, washed twice with water and brine. The organic layers were dried over MgSO4, filtered, evaporated and chromatographied (silica gel, AcOEt/heptane, 1/1) to give the title compound (450 mg, 70%).

Workup

  1. waitAfter 18 h at RT
  2. washwashed twice with water and brine
  3. dry with materialThe organic layers were dried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-ae8646a7205a40cbaf0b04f4e7d26ce2
Source dataset
uspto-grants-2010_03
Patent number
US07683079B2

Reaction notes

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