Cyclohexanecarboxaldehyde → HCID 69101439, compound

HRID 394012Notes

Reaction equation

HRID 394012 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][C:14]([NH:16][CH2:17][C@H:18]1[CH2:23][CH2:22][CH2:21][NH:20][CH2:19]1)=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([BH3-])#N.[Na+].[CH:28]1([CH:34]=O)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1>CO.C(OCC)(=O)C.[Cl-].[Zn+2].[Cl-]>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][C:14]([NH:16][CH2:17][C@H:18]1[CH2:23][CH2:22][CH2:21][N:20]([CH2:34][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)[CH2:19]1)=[O:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 16275CyclohexanecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 69100742HCID 69100742, compound

Product 1

HCID 69101439HCID 69101439, compound

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 600 mg of 3-(benzyloxycarbonyl)amino-N-{((3S)-3-piperidyl)methyl}propanamide in 3 ml of methanol, a solution of 150 mg of sodium cyanoborohydride and 160 mg of zinc chloride in 8.1 ml of methanol, and 0.30 ml of cyclohexanecarbaldehyde were added at room temperature, followed by an hour's stirring at the same temperature. The reaction liquid was diluted with ethyl acetate and successively washed with saturated aqueous sodium bicarbonate solution and saturated saline, followed by drying over anhydrous sodium sulfate. Upon distilling the solvent off under reduced pressure, 775 mg of the title compound was obtained.

Workup

  1. waitfollowed by an hour
  2. customThe reaction liquid
  3. washsuccessively washed with saturated aqueous sodium bicarbonate solution and saturated saline
  4. dry with materialby drying over anhydrous sodium sulfate
  5. distillationUpon distilling the solvent off under reduced pressure

Sources & evidence

ORD record
ord-bda88438554d4190a04f1d7c42eaba6b
Source dataset
uspto-grants-2004_10
Patent number
US06809108B1

Reaction notes

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