Benzyl 3-((3S)-3,4-dimethylpiperazin-1-yl)azetidine-1-carboxylate → (S)-4-(Azetidin-3-YL)-1,2-dimethylpiperazine
Reaction equation
[CH3:1][C@@H:2]1[N:7]([CH3:8])[CH2:6][CH2:5][N:4]([CH:9]2[CH2:12][N:11](C(OCC3C=CC=CC=3)=O)[CH2:10]2)[CH2:3]1>[C].[Pd].CO>[NH:11]1[CH2:12][CH:9]([N:4]2[CH2:5][CH2:6][N:7]([CH3:8])[C@@H:2]([CH3:1])[CH2:3]2)[CH2:10]1Participants
4
Procedure
To a mixed solution of benzyl 3-((3S)-3,4-dimethylpiperazin-1-yl)azetidine-1-carboxylate (28.6 g, 94.3 mmol) described in Production Example 4-2 and methanol (150 mL) was added 10% palladium-carbon (50% aqueous, 10.0 g) at room temperature. The resultant mixture was stirred under a hydrogen atmosphere at room temperature and at 0.35 MPa to 0.40 MPa for 1 hour and 45 minutes. The reaction mixture was purged with a nitrogen atmosphere, and then filtrated using Celite. A filtrate was concentrated under a reduced pressure to give the title compound (21.2 g, yield: quantitative). The product was used in the subsequent reaction without further purification.
Workup
- customThe reaction mixture was purged with a nitrogen atmosphere
- filtrationfiltrated
- concentrationA filtrate was concentrated under a reduced pressure
Sources & evidence
- ORD record
- ord-fb37f06564e6423bb10a6cdd1b11c5e6
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09174998B2
Reaction notes
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