benzyl (4S,10aR)-1,5-dioxodecahydropyrido[1,2-a][1,4]diazepin-4-ylcarbamate → (4S,10aR)-4-aminohexahydropyrido[1,2-a][1,4]diazepine-1,5(2H,7H)-dione
Reaction equation
[O:1]=[C:2]1[NH:8][CH2:7][C@H:6]([NH:9]C(=O)OCC2C=CC=CC=2)[C:5](=[O:20])[N:4]2[CH2:21][CH2:22][CH2:23][CH2:24][C@H:3]12>CCOC(C)=O.[Pd]>[NH2:9][C@@H:6]1[C:5](=[O:20])[N:4]2[CH2:21][CH2:22][CH2:23][CH2:24][C@@H:3]2[C:2](=[O:1])[NH:8][CH2:7]1Participants
4
Procedure
Argon was bubbled through a solution of benzyl (4S,10aR)-1,5-dioxodecahydropyrido[1,2-a][1,4]diazepin-4-ylcarbamate (37 mg, 0.11 mmol) in EtOAc (3 mL) for 5 min at rt. Then, 5% Pd/C (30 mg, 0.014 mmol) was added to the solution. The reaction mixture was stirred at rt under hydrogen (50 psi) for 3 hr. The reaction mixture was filtered through CELITE® and the filtrate was concentrated under reduced pressure to give (4S,10aR)-4-aminohexahydropyrido[1,2-a][1,4]diazepine-1,5(2H,7H)-dione (19 mg, 0.096 mmol, 86% yield) as a white solid. Anal. Calcd. for C9H15N3O2 m/z 197.2. found: 198.2 (M+H)+.
Workup
- filtrationThe reaction mixture was filtered through CELITE®
- concentrationthe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-f05c8eb1c8d84fa297a43239f410eec3
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09346852B2
Reaction notes
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