Triethylamine → (2S,6RS)-2,6-Dimethyl-3-oxo-piperazine-1-carboxylic acid benzyl ester

HRID 1432904Notes

Reaction equation

HRID 1432904 reaction equation
[CH3:1][C@@H:2]1[NH:7][CH:6]([CH3:8])[CH2:5][NH:4][C:3]1=[O:9].C(N(CC)CC)C.[CH2:17]([O:24][C:25](ON1C(=O)CCC1=O)=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(Cl)Cl>[CH2:17]([O:24][C:25]([N:7]1[CH:6]([CH3:8])[CH2:5][NH:4][C:3](=[O:9])[C@@H:2]1[CH3:1])=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 83172Benzyl succinimido carbonateHCID 45092763(3S, 5RS)-3,5-dimethyl-piperazin-2-one

Product 1

HCID 57066025(2S,6RS)-2,6-Dimethyl-3-oxo-piperazine-1-carboxylic acid benzyl esterYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3S, 5RS)-3,5-dimethyl-piperazin-2-one (24.3 mmol) in 100 mL of methylenechloride is added triethylamine (8.45 mL, 60.75 mmol) and N-(benzyloxycarbonyloxy)succinimide (12.1 g, 48.6 mmol). After stirring overnight, the CH2Cl2 is removed, and the crude mixture is chromatographed (50% EtOAc/Hexane). (2S, 6RS)-2,6-Dimethyl-3-oxo-piperazine-1-carboxylic acid benzyl ester (3.3 g, 52% yield over three steps) is isolated as a white powder. MS C14H18N2O3 MS m/z: 263.

Workup

  1. customthe CH2Cl2 is removed
  2. customthe crude mixture is chromatographed (50% EtOAc/Hexane)

Sources & evidence

ORD record
ord-6952f08852894ee380b50433edd9d28b
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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