Piperazin-2-one → HCID 18971567, compound

HRID 1894434Notes

Reaction equation

HRID 1894434 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][C:2]1=[O:7].[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([N:4]2[CH2:5][CH2:6][NH:1][C:2](=[O:7])[CH2:3]2)[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:9])[CH3:10]

Participants

5

Reactant 3

HCID 231360Piperazin-2-oneHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 18971567HCID 18971567, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The mixture of piperazin-2-one (1.11 g, 11.1 mmol, Aldrich), 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (2.43 g, 12.21 mmol, Aldrich) and sodium triacetoxyborohydride (2.59 g, 12.21 mmol, Aldrich) in dichloromethane (50 mL) was stirred at ambient temperature for 2 h. After the aqueous work up, the crude residue was purified by flash column chromatography (silica gel, Isco system, eluting with ethyl acetate and hexane) to give 4-(3-oxo-piperazin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (1.78 g).

Workup

  1. customAfter the aqueous work up, the crude residue was purified by flash column chromatography (silica gel, Isco system, eluting with ethyl acetate and hexane)

Sources & evidence

ORD record
ord-1548184021ff42da91b0908406da0761
Source dataset
uspto-grants-2013_08
Patent number
US08513239B2

Reaction notes

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