1-tert-Butyl 4-methyl 4-(cyanomethyl)piperidine-1,4-dicarboxylate → tert-Butyl 1-oxo-2,8-diazaspiro(4.5)decane-8-carboxylate

HRID 1501750Notes

Reaction equation

HRID 1501750 reaction equation
[C:1]([CH2:3][C:4]1([C:17]([O:19]C)=O)[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].[H][H]>CO.N.O.[Ni]>[O:19]=[C:17]1[C:4]2([CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]2)[CH2:3][CH2:1][NH:2]1

Participants

6

Reactant 2

HCID 713056681-tert-Butyl 4-methyl 4-(cyanomethyl)piperidine-1,4-dicarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 45073946tert-Butyl 1-oxo-2,8-diazaspiro(4.5)decane-8-carboxylate

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 12896473Azane;hydrateSolvent

Procedure

A suspension of 1-tert-butyl 4-methyl 4-(cyanomethyl)piperidine-1,4-dicarboxylate (70.0 g, 247.9 mmol) and Raney Ni (60 g) in MeOH (1500 mL) and NH3.H2O (80 mL) was stirred at 2 MPa of hydrogen pressure at 50° C. for 18 h. The reaction mixture was filtered through a pad of CELITE® and the filtrate was concentrated under vacuum to give a crude product, which was washed with ethyl acetate (200 mL) to give the title compound. 1H-NMR (400 MHz, CDCl3) δ 6.05 (s, 1H), 4.0 (s, 2H), 3.37-3.34 (m, 2H), 3.02-2.96 (m, 2H), 2.08-2.05 (m, 2H), 1.88-1.87 (m, 2H), 1.51-1.41 (m, 11H)

Workup

  1. filtrationThe reaction mixture was filtered through a pad of CELITE®
  2. concentrationthe filtrate was concentrated under vacuum
  3. customto give a crude product, which
  4. washwas washed with ethyl acetate (200 mL)

Sources & evidence

ORD record
ord-acc140a25cd44639a724351e3f9d1ba6
Source dataset
uspto-grants-2015_12
Patent number
US09206198B2

Reaction notes

Loading…