Tert-butyl 3-(azidomethyl)-4-(tert-butyldimethylsilyloxy)piperidine-1-carboxylate → Tert-butyl 3-(aminomethyl)-4-(tert-butyldimethylsilyloxy)piperidine-1-carboxylate

HRID 57545Notes

Reaction equation

HRID 57545 reaction equation
[N:1]([CH2:4][CH:5]1[CH:10]([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH2:9][CH2:8][N:7]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:6]1)=[N+]=[N-]>[Pd]>[NH2:1][CH2:4][CH:5]1[CH:10]([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH2:9][CH2:8][N:7]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:6]1

Participants

3

Reactant 1

HCID 71113754Tert-butyl 3-(azidomethyl)-4-(tert-butyldimethylsilyloxy)piperidine-1-carboxylate2×

Product 1

HCID 71113755Tert-butyl 3-(aminomethyl)-4-(tert-butyldimethylsilyloxy)piperidine-1-carboxylateYield 90%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The solution of tert-butyl 3-(azidomethyl)-4-(tert-butyldimethylsilyloxy)piperidine-1-carboxylate in ethyl acetate from step C was hydrogenated under hydrogen atmosphere with 10% Pd/C (500 mg) overnight. The catalyst was filtered and the filtrate was concentrated under reduced pressure to give the title compound (6.2 g, 90% yield). MS (m/z): 345 (M+H)+.

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-988634ce3f944010b1882f3f241a6f9e
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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