HCID 66660976, compound → HCID 66660862, compound

HRID 1019705Notes

Reaction equation

HRID 1019705 reaction equation
[C:1]([CH2:3][C:4]1([CH2:17][CH:18]([CH3:20])[CH3:19])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)#[N:2]>[Ni].CO>[NH2:2][CH2:1][CH2:3][C:4]1([CH2:17][CH:18]([CH3:20])[CH3:19])[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[CH2:8][CH2:9]1

Participants

4

Reactant 1

HCID 66660976HCID 66660976, compound

Product 1

HCID 66660862HCID 66660862, compoundYield 44.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

The process is performed according to the procedure described in Example 12 (step 12.2.). Starting with 1.10 g (3.95 mmol) of tert-butyl 4-cyanomethyl-4-isobutylpiperidine-1-carboxylate and 1.16 g (19.75 mmol) of Raney nickel in 13 mL of methanol under a hydrogen atmosphere (70 psi), at 45° C. and after chromatography on a column of silica gel, eluting with a 96/4/0.4 mixture of dichloromethane, methanol and 28% aqueous ammonia, 0.50 g of expected product is obtained in the form of an oil.

Workup

  1. washat 45° C. and after chromatography on a column of silica gel, eluting with a 96/4/0.4 mixture of dichloromethane, methanol and 28% aqueous ammonia

Sources & evidence

ORD record
ord-b7a4cb5c7c2440109bd9e314054ed03c
Source dataset
uspto-grants-2014_05
Patent number
US08716289B2

Reaction notes

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