tert-butyl (4S,7S,10aS)-5-oxo-7-vinyloctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamate → tert-butyl (4S,7R,10aS)-7-ethyl-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamate
Reaction equation
[O:1]=[C:2]1[C@@H:8]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:7][CH2:6][S:5][C@H:4]2[CH2:17][CH2:18][CH2:19][C@@H:20]([CH:21]=[CH2:22])[N:3]12.[H][H]>CO.[Pd]>[CH2:21]([C@H:20]1[N:3]2[C@@H:4]([S:5][CH2:6][CH2:7][C@H:8]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[C:2]2=[O:1])[CH2:17][CH2:18][CH2:19]1)[CH3:22]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of tert-butyl (4S,7S,10aS)-5-oxo-7-vinyloctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamate (66 mg, 0.20 mmol) in MeOH (2 mL) was purged with argon for 2 min. Then, 10% Pd/C (80 mg, 0.75 mmol) was added. The reaction mixture was stirred for under a hydrogen balloon for 3 days. The reaction mixture was filtered. The filtrate was concentrated and dried under the high vacuum to give tert-butyl (4S,7R,10 aS)-7-ethyl-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamate (52 mg, 0.16 mmol, 78% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 6.02 (d, J=5.5 Hz, 1H), 5.39-5.15 (m, 1H), 4.92-4.66 (m, 1H), 4.53-4.30 (m, 1H), 3.38-3.14 (m, 1H), 2.97-2.66 (m, 1H), 2.46-2.20 (m, 1H), 2.15-1.62 (m, 8H), 1.62-1.35 (m, 10H), 0.93 (t, J=7.4 Hz, 3H).
Workup
- filtrationThe reaction mixture was filtered
- concentrationThe filtrate was concentrated
- customdried under the high vacuum
Sources & evidence
- ORD record
- ord-18db51e0da554f82be3bf12f3fa9d00d
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09346852B2
Reaction notes
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