Sodium Hydroxide → tert-Butyl 2-(aminomethyl)-6-azaspiro[3.4]octane-6-carboxylate

HRID 336531Notes

Reaction equation

HRID 336531 reaction equation
[C:1]([CH:3]1[CH2:6][C:5]2([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7]2)[CH2:4]1)#[N:2].[OH-].[Na+]>[Ni].C(O)C>[NH2:2][CH2:1][CH:3]1[CH2:4][C:5]2([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7]2)[CH2:6]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 56962170Tert-butyl 2-cyano-6-azaspiro[3.4]octane-6-carboxylate

Product 1

HCID 68001449tert-Butyl 2-(aminomethyl)-6-azaspiro[3.4]octane-6-carboxylate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Raney nickel is added in catalytic amount to a solution of 0.27 g (1.14 mmol) of tert-butyl 2-cyano-6-azaspiro[3.4]octane-6-carboxylate (isomer 1a), obtained in step 8.1., in 10 mL of a 1N solution of sodium hydroxide in ethanol. The reaction medium is placed in a Parr flask under a hydrogen atmosphere (4 bar), at room temperature for 5 hours.

Workup

  1. customobtained in step 8.1

Sources & evidence

ORD record
ord-feb8fcb3084044cd90bcdf9089cc41ec
Source dataset
uspto-grants-2014_11
Patent number
US08889702B2

Reaction notes

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