Ammonia → Tert-butyl 4-[(2R)-3-amino-2-hydroxy-propyl]piperazine-1-carboxylate

HRID 2364706Notes

Reaction equation

HRID 2364706 reaction equation
[O:1]1[CH2:3][C@@H:2]1[CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1.[NH3:18]>C(O)C>[NH2:18][CH2:3][C@@H:2]([OH:1])[CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 10977626(S)-1-Boc-4-(oxiran-2-ylmethyl)piperazine

Product 1

HCID 7009319Tert-butyl 4-[(2R)-3-amino-2-hydroxy-propyl]piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Tert-butyl 4-[[(2S)-oxiran-2-yl]methyl]piperazine-1-carboxylate 20a (9.20 g, 38 mmol) was dissolved in 60 mL of ethanol followed by the addition of 50 mL of aqueous ammonia. The reaction solution was stirred for 12 hours. The reaction solution was concentrated under reduced pressure to obtain the crude title compound tert-butyl 4-[(2R)-3-amino-2-hydroxy-propyl]piperazine-1-carboxylate 20b (9 g, as a white solid), which was used in the next step without further furification.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-363af2e17a5f48d398d140b3d74d5a9f
Source dataset
uspto-grants-2014_04
Patent number
US08691822B2

Reaction notes

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