Ammonia → Tert-butyl 4-(3-aminopropyl)-4-methylpiperidine-1-carboxylate

HRID 1986186Notes

Reaction equation

HRID 1986186 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](/[CH:15]=[CH:16]/[C:17]#[N:18])([CH3:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N.[H][H]>C(O)C.[Rh]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:15][CH2:16][CH2:17][NH2:18])([CH3:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 68857538trans-4-(2-Cyanovinyl)-4-methylpiperidine-1-carboxylic acid tert-butyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 68857055Tert-butyl 4-(3-aminopropyl)-4-methylpiperidine-1-carboxylateYield 63.4%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 702EthanolSolvent

Procedure

Cis/trans-4-(2-cyanovinyl)-4-methylpiperidine-1-carboxylic acid tert-butyl ester (1.00 g, 4.0 mmol), 5% Rh/Al2O3 (0.500 g) and 28% aqueous NH3 (1.25 mL) are heated at 35° C. in ethanol (20 mL) and 50 psi hydrogen gas for 18 hours. The reaction mixture is filtered through Celite®, concentrated, and chromatographed with 0-20% (2M NH3 in MeOH) in dichloromethane to give the title compound as a clear oil (0.65 g, 63% yield).

Workup

  1. filtrationThe reaction mixture is filtered through Celite®
  2. concentrationconcentrated
  3. customchromatographed with 0-20% (2M NH3 in MeOH) in dichloromethane

Sources & evidence

ORD record
ord-8b342d06199d4a3c875f8672994238f5
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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