Sodium Hydroxide → HCID 68430082, compound
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[C:20](=O)[C:19]2[CH:22]=[CH:23][C:24]([S:26][CH:27]([CH3:29])[CH3:28])=[N:25][C:18]=2[O:17][CH2:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-].[Na+].[Cl-].[NH4+]>C(OCC)C.O>[CH2:7]([N:14]1[CH2:20][C:19]2[CH:22]=[CH:23][C:24]([S:26][CH:27]([CH3:29])[CH3:28])=[N:25][C:18]=2[O:17][CH2:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1Participants
Procedure
To a mixture of lithium aluminum hydride (0.061 g) and diethyl ether (2.0 mL) was added a solution of the compound obtained in step 1 (0.35 g) in diethyl ether (3.0 mL), and the resulting mixture was stirred at room temperature for 2 hr under a nitrogen atmosphere. 1N Aqueous sodium hydroxide solution (0.061 mL), saturated aqueous ammonium chloride (0.061 mL) and water (0.061 mL) were added, and the resulting mixture was stirred at room temperature for 3 hr. The precipitate was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (25% ethyl acetate/hexane) to give 4-benzyl-8-(isopropylthio)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (0.26 g, 79%) as a colorless oil.
Workup
- stirringthe resulting mixture was stirred at room temperature for 3 hr
- customThe precipitate was removed by filtration
- concentrationthe filtrate was concentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (25% ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-a635f8db3ea7455f8a8918f5599077b7
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08329687B2
Reaction notes
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