Reaction equation
[CH2:1]([CH:8]1[C:16]2[C:11](=[CH:12][C:13]([F:19])=[C:14]([C:17]#[N:18])[CH:15]=2)[CH2:10][CH:9]1[NH:20][C:21](=[O:25])[O:22][CH2:23][CH3:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].[H][H]>CO.O.O.O.O.O.O.[Co](Cl)Cl>[NH2:18][CH2:17][C:14]1[CH:15]=[C:16]2[C:11]([CH2:10][CH:9]([NH:20][C:21](=[O:25])[O:22][CH2:23][CH3:24])[CH:8]2[CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:12][C:13]=1[F:19]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of ethyl 1-benzyl-6-cyano-5-fluoro-2,3-dihydro-1H-inden-2-ylcarbamate (182 mg, 0.538 mmol) in methanol (5 ml) containing cobalt(II) chloride hexahydrate (256 mg, 1.076 mmol) was added sodium borohydride (203 mg, 5.38 mmol) in small portions with caution to control the evolution of hydrogen and the exothermic reaction (approximately 1 h). The reaction mixture was stirred at room temperature for 10 min and carefully quenched by addition of 12N hydrochloric acid until the black precipitate was dissolved. The reaction mixture was carefully made alkaline with concentrated ammonia and extracted with ethyl acetate, dried, filtered and evaporated to leave the crude product ethyl 6-(aminomethyl)-1-benzyl-5-fluoro-2,3-dihydro-1H-inden-2-ylcarbamate a pale brown oil. m=184 mg (quant.)
Workup
- customthe exothermic reaction (approximately 1 h)
- customcarefully quenched by addition of 12N hydrochloric acid until the black precipitate
- dissolutionwas dissolved
- extractionextracted with ethyl acetate
- customdried
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-535d4b8c466749d39d03aee7f799d264
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846743B2
Linked notes
Loading…