1,2-Dichloroethane → tert-Butyl cis(+/-)-4-(benzylamino)-[(2E)-2-buten-1-yloxy]piperidine-1-carboxylate

HRID 43684Notes

Reaction equation

C(O[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)/C=C/C.[CH2:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(O[BH-](O[C:38](=[O:40])[CH3:39])OC(=O)C)(=O)C.[Na+].Cl[CH2:43][CH2:44]Cl>>[CH2:20]([NH:27][C@H:11]1[CH2:6][CH2:7][N:8]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[C@@H:9]([O:40][CH2:38]/[CH:39]=[CH:43]/[CH3:44])[CH2:10]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

Reactant 4

HCID 111,2-Dichloroethane

HCID 7504Benzylamine

HCID 5049666Sodium triacetoxyborohydride

HCID 67548695tert-Butyl 3-[(2E)-2-buten-1-yloxy]-4-oxopiperidine-1-carboxylate

Product 1

HCID 86648623tert-Butyl cis(+/-)-4-(benzylamino)-[(2E)-2-buten-1-yloxy]piperidine-1-carboxylateYield 99%

Procedure

The same operation as in Example (90c) was performed using tert-butyl 3-[(2E)-2-buten-1-yloxy]-4-oxopiperidine-1-carboxylate obtained in Example (119b) (5 g, 16 mmol), benzylamine (2.04 g, 19 mmol), sodium (triacetoxy)borohydride (7.41 g, 35 mmol) and 1,2-dichloroethane (50 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 5.74 g of the title compound as a colorless solid (99%).

Workup

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-1478f796eba04961951eebd0f4c3c6e7
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536197B2

Reaction notes

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