Benzylamine → tert-Butyl cis(+/-)-4-(benzylamino)-3-allyloxypiperidine-1-carboxylate

HRID 1425134Notes

Reaction equation

HRID 1425134 reaction equation
[CH2:1]([O:4][CH:5]1[C:10](=O)[CH2:9][CH2:8][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6]1)[CH:2]=[CH2:3].[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:19]([NH:26][C@H:10]1[CH2:9][CH2:8][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][C@H:5]1[O:4][CH2:1][CH:2]=[CH2:3])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 67548846tert-Butyl 3-allyloxy-4-oxopiperidine-1-carboxylate

Product 1

HCID 86648602tert-Butyl cis(+/-)-4-(benzylamino)-3-allyloxypiperidine-1-carboxylateYield 83.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The same operation as in Example (90c) was performed using tert-butyl 3-allyloxy-4-oxopiperidine-1-carboxylate obtained in Example (113b) (4.37 g, 17.1 mmol), benzylamine (2.02 g, 18.9 mmol), sodium (triacetoxy)borohydride (6.36 g, 30 mmol) and 1,2-dichloroethane (40 mL). The resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=4/1, 1/1, 1/3, 0/1) to obtain 4.96 g of the title compound as a colorless oily substance (84%).

Workup

  1. customThe resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=4/1, 1/1, 1/3, 0/1)

Sources & evidence

ORD record
ord-1f227f7a3a6d44b2a266118620d07d27
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

Loading…