Ethyl 4-piperidinecarboxylate → 1-(3,3-Dimethyl-butyl)-piperidine-4-carboxylic Acid Ethyl Ester

HRID 220800Notes

Reaction equation

HRID 220800 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[CH2:3][CH:4]=O.[NH:8]1[CH2:18][CH2:17][CH:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:10][CH2:9]1.C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[CH2:15]([O:14][C:12]([CH:11]1[CH2:17][CH2:18][N:8]([CH2:4][CH2:3][C:2]([CH3:7])([CH3:6])[CH3:1])[CH2:9][CH2:10]1)=[O:13])[CH3:16]

Participants

5

Reactant 3

HCID 70770Ethyl 4-piperidinecarboxylateHCID 763353,3-DimethylbutanalHCID 5003444Sodium cyanoborohydride

Product 1

HCID 606927891-(3,3-Dimethyl-butyl)-piperidine-4-carboxylic Acid Ethyl EsterYield 71%

Reagents, catalysts & solvents 1

HCID 10129899Acetic acid methanolSolvent

Procedure

3,3-Dimethylbutyraldehyde (5.26 ml, 42.0 mmol) was added to a solution of ethyl isonipecotate (6.6 g, 42.0 mmol) in methanol/acetic acid (99:1, v/v, 50 ml) and the mixture was stirred at room temperature for 1 h. Sodium cyanoborohydride (3.43 g, 54.6 mmol) was added, and the mixture was stirred at room temperature for 4 days then concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 25% EtOAc:75% cyclohexane) to yield the title compound (7.16 g, 71%).

Workup

  1. stirringthe mixture was stirred at room temperature for 4 days
  2. concentrationthen concentrated in vacuo
  3. customThe residue was purified by flash chromatography on silica gel (eluant; 25% EtOAc:75% cyclohexane)

Sources & evidence

ORD record
ord-55aac7d60f2a4d33b08a1c199aea8610
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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