Ammonia → tert-butyl 4-[(2S)-3-amino-2-hydroxy-propyl]piperazine-1-carboxylate
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]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
Tert-butyl 4-[[(2R)-oxiran-2-yl]methyl]piperazine-1-carboxylate 7b (3.55 g, 14.70 mmol) was dissolved in 40 mL of ethanol followed by the addition of 40 mL of aqueous ammonia, stirred for 12 hours. The resulting solution was heated to 50° C. and stirred for another 1 hour, then concentrated under reduced pressure to obtain the crude title compound tert-butyl 4-[(2S)-3-amino-2-hydroxy-propyl]piperazine-1-carboxylate 7c (3.40 g) as a light yellow solid, which was used in the next step without further furification.
Workup
- stirringstirred for another 1 hour
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-a6815d09190c420f9a36eab9d568d9cb
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08691822B2
Reaction notes
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