Hydrochloric Acid → (+/-)-3-Butyl-3-ethyl-2,3,4,5-tetrahydro-1,4-benzothiazepine
Reaction equation
[CH2:1]([C:5]1([CH2:17][CH3:18])[NH:11][C:10](=O)[C:9]2[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=2[S:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].B#B.Cl>O1CCCC1>[CH2:1]([C:5]1([CH2:17][CH3:18])[NH:11][CH2:10][C:9]2[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=2[S:7][CH2:6]1)[CH2:2][CH2:3][CH3:4]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
A solution of the product from step (a) (46.5 g,) in tetrahydrofuran (260 ml) was cooled to 0° C., and 1M diborane (450 ml, Aldrich) in THF was slowly added. The resulting mixture was heated to reflux for 48 hours, cooled to 0° C., and treated carefully with 6M aqueous HCl. The mixture was heated to reflux for 1.5 hours, concentrated to 400 ml and extracted twice with diethyl ether. The organic layers were dried and concentrated to afford the title product (44.0 g) as a colorless oil. 1H NMR consistent with the proposed structure.
Workup
- temperatureThe resulting mixture was heated
- temperatureto reflux for 48 hours
- temperatureThe mixture was heated
- temperatureto reflux for 1.5 hours
- concentrationconcentrated to 400 ml
- extractionextracted twice with diethyl ether
- customThe organic layers were dried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-7f501b749b3c490a8ee92a59f799ef8f
- Source dataset
- uspto-grants-1998_10
- Patent number
- US05817652
Reaction notes
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