Hydrochloric Acid → 1-[N-ethyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-methoxy-1H-indene
Reaction equation
[C:1]([N:4]([CH:23]1[C:31]2[C:26](=[C:27]([O:32][CH3:33])[CH:28]=[CH:29][CH:30]=2)[CH2:25][CH2:24]1)[CH2:5][C:6]1[O:7][C:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:10]=1)(=O)[CH3:2].Cl>C1COCC1>[CH2:1]([N:4]([CH:23]1[C:31]2[C:26](=[C:27]([O:32][CH3:33])[CH:28]=[CH:29][CH:30]=2)[CH2:25][CH2:24]1)[CH2:5][C:6]1[O:7][C:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:9]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:10]=1)[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 1-[N-acetyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-methoxy-1H-indene (0.40 g) in THF (10 ml) was added 1M solution of borane-THF complex in THF (9 ml) at room temperature. The reaction mixture was refluxed for 8 hours and cooled down to room temperature. 1N aqueous HCl solution (25 ml) was added to the reaction mixture. After being stirred for 1 hour at room temperature, the mixture was partitioned between ethyl acetate and 1N aqueous NaOH solution. The organic layer was washed with brine. The dried solvent was evaporated in vacuo to give 1-[N-ethyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-methoxy-1H-indene (0.47 g).
Workup
- temperatureThe reaction mixture was refluxed for 8 hours
- customthe mixture was partitioned between ethyl acetate and 1N aqueous NaOH solution
- washThe organic layer was washed with brine
- customThe dried solvent was evaporated in vacuo
Sources & evidence
- ORD record
- ord-f402e5e0161747cca54d4efaa13bda53
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06300344B1
Reaction notes
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