Tetrahydrofuran → di-tert-butyl (2S)-2-(((3S)-3-methyl-4-morpholinyl)methyl)-1,4-piperazinedicarboxylate
Reaction equation
[CH3:1][C@H:2]1[CH2:7][O:6][CH2:5][CH2:4][N:3]1[C:8]([C@H:10]1[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13][CH2:12][N:11]1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=O.B.C1COCC1.C1COCC1>CO>[CH3:1][C@H:2]1[CH2:7][O:6][CH2:5][CH2:4][N:3]1[CH2:8][C@H:10]1[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:13][CH2:12][N:11]1[C:23]([O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:24]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A 250-mL round-bottomed flask was charged with di-tert-butyl (2R)-2-(((3S)-3-methyl-4-morpholinyl)carbonyl)-1,4-piperazinedicarboxylate (2.55 g, 6.17 mmol, step 1), BH3.THF (1.0 M in THF, 19.0 mL, 19.0 mmol, Sigma-Aldrich, St. Louis, Mo.) and THF (100 mL). The mixture was stirred at 50° C. for 15 h. The mixture was allowed to cool to room temperature and then additional BH3.THF complex (1.0 M in THF, 5.0 mL, 5.0 mmol) was added. The reaction mixture was heated at 50° C. for 1 h. The mixture was allowed to cool to room temperature and then MeOH was added slowly until bubbling ceased. The reaction mixture was concentrated to give di-tert-butyl (2S)-2-(((3S)-3-methyl-4-morpholinyl)methyl)-1,4-piperazinedicarboxylate (2.5 g) as a white solid.
Workup
- temperatureto cool to room temperature
- temperatureThe reaction mixture was heated at 50° C. for 1 h
- temperatureto cool to room temperature
- customuntil bubbling
- concentrationThe reaction mixture was concentrated
Sources & evidence
- ORD record
- ord-ddfde06b44c042419959ad992a9652b1
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08431563B2
Reaction notes
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