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

HRID 43707Notes

Reaction equation

HRID 43707 reaction equation
[F:1][CH2:2][CH2:3][CH2:4][O:5][CH:6]1[C:11](=O)[CH2:10][CH2:9][N:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:7]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:11]1[CH2:10][CH2:9][N:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:7][C@H:6]1[O:5][CH2:4][CH2:3][CH2:2][F:1])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 68406217HCID 68406217, compound

Product 1

HCID 86648651tert-Butyl cis(+/-)-4-(benzylamino)-3-(3-fluoropropoxy)piperidine-1-carboxylateYield 86.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The same operation as in Example (90c) was performed using tert-butyl 3-(3-fluoropropoxy)-4-oxopiperidine-1-carboxylate obtained in Example (127b) (1.71 g, 6.21 mmol), benzylamine (0.75 g, 7 mmol), sodium (triacetoxy)borohydride (2.54 g, 12 mmol) and 1,2-dichloroethane (20 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 1.97 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-4860c38335cc44368d7e3e1c86e9023d
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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