tert-Butyl piperazine-1-carboxylate → (S)-1-Boc-4-(oxiran-2-ylmethyl)piperazine

HRID 555304Notes

Reaction equation

HRID 555304 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O:14]1[CH2:16][C@@H:15]1[CH2:17]OS(C1C=CC=C([N+]([O-])=O)C=1)(=O)=O>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:17][C@H:15]2[CH2:16][O:14]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 146513Benzenesulfonic acid, 3-nitro-, (2R)-2-oxiranylmethyl ester

Product 1

HCID 10977626(S)-1-Boc-4-(oxiran-2-ylmethyl)piperazineYield 70%

Procedure

The same method as employed in the preparation of Intermediate 1 but starting from piperazine-1-carboxylic acid tert-butyl ester and (R)-(−)-3-nitro-benzenesulfonic acid oxiranylmethyl ester gives after flash chromatography the title compound as a yellow oil in a 70% yield.

Sources & evidence

ORD record
ord-41f78fbc52514ee69b8ce663b3f928ed
Source dataset
uspto-grants-2011_11
Patent number
US08053436B1

Reaction notes

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