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

HRID 43649Notes

Reaction equation

HRID 43649 reaction equation
[CH2:1]([O:3][CH:4]1[C:9](=O)[CH2:8][CH2:7][N:6]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:5]1)[CH3:2].[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:18]([NH:25][C@H:9]1[CH2:8][CH2:7][N:6]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:5][C@H:4]1[O:3][CH2:1][CH3:2])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 68406177Tert-butyl 3-ethoxy-4-oxopiperidine-1-carboxylate

Product 1

HCID 86648597tert-Butyl cis(+/-)-4-(benzylamino)-3-ethoxypiperidine-1-carboxylateYield 86.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The same operation as in Example (90c) was performed using tert-butyl 3-ethoxy-4-oxopiperidine-1-carboxylate obtained in Example (90b) (3.4 g, 14 mmol), benzylamine (1.65 g, 15.4 mmol), sodium (triacetoxy)borohydride (5.93 g, 28 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 4.06 g of the title compound as a colorless oily substance (87%).

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-b24c6aeb716845e09f2ea0018becade1
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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