Ammonium Chloride → (Rac)-(7r,8r,10as)-6-chloro-3,7,8,9,10,11-hexahydro-8,10a-methanoazuleno-[2,1-e]indazol-7-ol
Reaction equation
[Cl:1][C:2]1[C:3](=[O:20])[CH:4]2[CH2:19][C:7]3([C:18]=1[C:17]1[CH:16]=[CH:15][C:14]4[NH:13][N:12]=[CH:11][C:10]=4[C:9]=1[CH2:8]3)[CH2:6][CH2:5]2.[BH4-].[Na+].[Cl-].[NH4+]>CCO>[Cl:1][C:2]1[C@H:3]([OH:20])[C@H:4]2[CH2:19][C@@:7]3([C:18]=1[C:17]1[CH:16]=[CH:15][C:14]4[NH:13][N:12]=[CH:11][C:10]=4[C:9]=1[CH2:8]3)[CH2:6][CH2:5]2Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirring suspension of 6-chloro-3,9,10,11-tetrahydro-8,10a -methanoazuleno[2,1-e]indazol-7(8H)-one (305 mg, 1.07 mmol) in EtOH (30 mL) was added sodium borohydride (122 mg, 3.2 mmol) at room temperature. A bright yellow color appeared shortly after this addition and with time the reaction mixture became homogeneous. The reaction mixture was stirred at room temperature for 3 hours after which saturated aqueous ammonium chloride was added in portions until bubbling stopped. The reaction mixture was then diluted with ethyl acetate and washed with water followed by brine. The organic phase was dried over sodium sulfate, filtered through a small pad of silica gel, and then concentrated under vacuum to yield (rac)-(7R,8R,10aS)-6-chloro-3,7,8,9,10,11-hexahydro-8,10a-methanoazuleno-[2,1-e]indazol-7-ol as a faintly yellow solid.
Workup
- additionafter this addition
- additionwas added in portions
- customuntil bubbling
- additionThe reaction mixture was then diluted with ethyl acetate
- washwashed with water
- dry with materialThe organic phase was dried over sodium sulfate
- filtrationfiltered through a small pad of silica gel
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-cb3bc7d041f743398b46d705f3b89d04
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07923568B2
Reaction notes
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