Acetic Acid → HCID 10520795, compound

HRID 1054027Notes

Reaction equation

HRID 1054027 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:3][CH2:2]1.[N+:15]([C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH:21]=O)([O-:17])=[O:16].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(O)(=O)C>CO>[N+:15]([C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH2:21][N:1]1[CH2:2][CH2:3][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[CH2:5][CH2:6]1)([O-:17])=[O:16]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 74493-NitrobenzaldehydeHCID 7238334-(N-Boc-amino)piperidineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 10520795HCID 10520795, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
30 °C

Procedure

To a mixture of tert-butyl N-(piperidin-4-yl)carbamate (25 g, 125 mmol, 1.0 eq) and 3-nitrobenzaldehyde (19 g, 125 mmol, 1.0 eq) in MeOH (500 mL) were added NaBH(OAc)3 (53 g, 250 mmol, 2.0 eq) and acetic acid (1 mL). Then the resulting mixture was stirred at 30° C. overnight. LC-MS indicated complete conversion. The solvent was removed under vaccum and the residue was purified by column chromatography (DCM:MeOH=15:1), to provide tert-butyl N-{1-(3-nitrobenzyl)piperidin-4-yl}carbamate (32 g, 76%) as a white solid.

Workup

  1. customThe solvent was removed under vaccum
  2. customthe residue was purified by column chromatography (DCM:MeOH=15:1)

Sources & evidence

ORD record
ord-7ca5e76b59694d688e4069dfff2756dc
Source dataset
uspto-grants-2016_07
Patent number
US09394286B2

Reaction notes

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