Aluminium lithium hydride → 1,2,3,4-Tetrahydro-7-phenylmethoxy-4-methycyclopent[b]indole-2-methanol
Reaction equation
C([O:3][C:4]([CH:6]1[CH2:26][C:9]2[N:10]([CH3:25])[C:11]3[CH:12]=[CH:13][C:14]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:15][C:16]=3[C:8]=2[CH2:7]1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[C:19]1([CH2:18][O:17][C:14]2[CH:13]=[CH:12][C:11]3[N:10]([CH3:25])[C:9]4[CH2:26][CH:6]([CH2:4][OH:3])[CH2:7][C:8]=4[C:16]=3[CH:15]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a solution of 1,2,3,4-tetrahydro-7-phenylmethoxy-4-methycyclopent[b]indole-2-carboxylic acid ethyl ester (2.0 g, 0.006 mole) in 50 ml of dry tetrahydrofuran, was added lithium aluminum hydride (1M solution in tetrahydrofuran, 10 ml, 0.01 mole). After stirring at 70° C. for one hour, the mixture was cooled, quenched with 2 ml of saturated ammonium chloride solution, filtered, and the filtrate concentrated to a brown oil, ~2 g. This oil was eluted on a silica gel column with 10% methanol/dichloromethane via HPLC. The desired fractions were combined and concentrated to a tan oil, which solidified on standing to give 1.3 g of the product, m.p. 83°-85° C.
Workup
- temperaturethe mixture was cooled
- customquenched with 2 ml of saturated ammonium chloride solution
- filtrationfiltered
- concentrationthe filtrate concentrated to a brown oil, ~2 g
- washThis oil was eluted on a silica gel column with 10% methanol/dichloromethane via HPLC
- concentrationconcentrated to a tan oil, which
Sources & evidence
- ORD record
- ord-ec0f9592505e45bdb33ea398a1dd417e
- Source dataset
- uspto-grants-1994_09
- Patent number
- US05350762
Reaction notes
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