tert-Butyl piperazine-1-carboxylate → tert-butyl 4-[(2S)-3-benzyloxycarbonylamino-2-hydroxy-propyl]piperazine-1-carboxylate

HRID 1525128Notes

Reaction equation

HRID 1525128 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:14]([O:21][C:22](=[O:28])[NH:23][CH2:24][C@H:25]1[CH2:27][O:26]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[C:4]([O:3][C:1]([N:8]1[CH2:9][CH2:10][N:11]([CH2:27][C@@H:25]([OH:26])[CH2:24][NH:23][C:22]([O:21][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:28])[CH2:12][CH2:13]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

3

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 10375722(S)-oxiranylmethyl-carbamic acid benzyl ester

Product 1

HCID 68107178tert-butyl 4-[(2S)-3-benzyloxycarbonylamino-2-hydroxy-propyl]piperazine-1-carboxylateYield 37%

Procedure

The compound was prepared in analogy to Example 17, step 17.1, starting from 1-Boc-piperazine (20.41 g) and [(2S)-oxiranylmethyl]-carbamic acid benzyl ester (22.75 g). A yellowish oil (16.0 g; 37% yield) was obtained.

Workup

  1. customThe compound was prepared in analogy to Example 17, step 17.1
  2. customA yellowish oil (16.0 g; 37% yield) was obtained

Sources & evidence

ORD record
ord-13840e0443394307be43e3fbd547d4b4
Source dataset
uspto-grants-2015_07
Patent number
US09079922B2

Reaction notes

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