Tert-butyl 4-(cyanomethyl)-4-methylpiperidine-1-carboxylate → Tert-butyl 4-(2-aminoethyl)-4-methylpiperidine-1-carboxylate

HRID 1986180Notes

Reaction equation

HRID 1986180 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:15][C:16]#[N:17])([CH3:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>O.C(O)C.N.[Rh]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:15][CH2:16][NH2:17])([CH3:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 2

HCID 66660780Tert-butyl 4-(cyanomethyl)-4-methylpiperidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 66660873Tert-butyl 4-(2-aminoethyl)-4-methylpiperidine-1-carboxylateYield 50%

Reagents, catalysts & solvents 4

HCID 23948RhodiumCatalystHCID 222AmmoniaSolventHCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To 5% Rh/Al2O3 (0.600 g) suspended in water (2 mL) is added ethanol (5 mL), 4-cyanomethyl-4-methylpiperidine-1-carboxylic acid tert-butyl ester (0.258 g, 1.083 mmol) dissolved in ethanol (10 mL) and 28% NH3 (aq) (0.25 mL). The reaction mixture is subjected to 50 psi hydrogen gas and stirred at room temperature for 18 hours. The reaction mixture is filtered to remove the catalyst, then the filtrate is concentrated and chromatographed on silica gel, eluting with 0-10% (2 M NH3 in MeOH) in dichloromethane to give the title compound (130 mg, 50% yield).

Workup

  1. filtrationThe reaction mixture is filtered
  2. customto remove the catalyst
  3. concentrationthe filtrate is concentrated
  4. customchromatographed on silica gel
  5. washeluting with 0-10% (2 M NH3 in MeOH) in dichloromethane

Sources & evidence

ORD record
ord-6d8aea29b38a4ce88493911db2c68e8f
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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