Benzylamine → tert-Butyl cis(+/-)-4-(benzylamino)-3-[(2-methyl-2-propen-1-yl)oxy]piperidine-1-carboxylate

HRID 43679Notes

Reaction equation

HRID 43679 reaction equation
[CH3:1][C:2](=[CH2:19])[CH2:3][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.[CH2:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:20]([NH:27][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][CH2:3][C:2]([CH3:1])=[CH2:19])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 67549026tert-Butyl 3-[(2-methyl-2-propen-1-yl)oxy]-4-oxopiperidine-1-carboxylate

Product 1

HCID 86648620tert-Butyl cis(+/-)-4-(benzylamino)-3-[(2-methyl-2-propen-1-yl)oxy]piperidine-1-carboxylateYield 78.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The same operation as in Example (90c) was performed using tert-butyl 3-[(2-methyl-2-propen-1-yl)oxy]-4-oxopiperidine-1-carboxylate obtained in Example (117b) (3.43 g, 17.1 mmol), benzylamine (1.5 g, 14 mmol), sodium (triacetoxy)borohydride (4 g, 18.9 mmol) and 1,2-dichloroethane (30 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 3.97 g of the title compound as a colorless oily substance (86%).

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-ecd09388da574ae399447b43fefcf25b
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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