Aluminium lithium hydride → (RS,SR)-2-(1-benzenesulfonyl-2-hydroxy-1-methyl-ethyl)-7-chloro-2,3-dihydro-1H-cyclopenta[b]indole-4-carboxylic acid tert-butyl ester

HRID 602805Notes

Reaction equation

HRID 602805 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[CH:15]=[CH:14][C:13]([Cl:17])=[CH:12][C:11]=2[C:10]2[CH2:18][CH:19]([C:21]([S:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)(=[O:29])=[O:28])([C:23](OC)=[O:24])[CH3:22])[CH2:20][C:9]1=2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[C:16]2[CH:15]=[CH:14][C:13]([Cl:17])=[CH:12][C:11]=2[C:10]2[CH2:18][CH:19]([C:21]([S:27]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)(=[O:28])=[O:29])([CH3:22])[CH2:23][OH:24])[CH2:20][C:9]1=2)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67266834(RS,SR)-2-(1-benzenesulfonyl-1-methoxycarbonyl-ethyl)-7-chloro-2,3-dihydro-1H-cyclopenta[b]indole-4-carboxylic acid tert-butyl ester

Product 1

HCID 67267940(RS,SR)-2-(1-benzenesulfonyl-2-hydroxy-1-methyl-ethyl)-7-chloro-2,3-dihydro-1H-cyclopenta[b]indole-4-carboxylic acid tert-butyl esterYield 35.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

152 mg (0.29 mmol) (RS,SR)-2-(1-benzenesulfonyl-1-methoxycarbonyl-ethyl)-7-chloro-2,3-dihydro-1H-cyclopenta[b]indole-4-carboxylic acid tert-butyl ester were dissolved in 3 mL dry THF at RT. 0.32 mL (0.32 mmol, 1.1 eq) of LiAlH4 (1M in THF) were added dropwise. The reaction mixture was stirred for 1 hour and 40 minutes. The reaction was quenched with a saturated NaHCO3 solution. The organic phase was washed with brine, dried over Na2SO4, filtered and evaporated. Column chromatography on silica gel (EtOAc/heptane 1:2) yielded 50 mg (35%) (RS,SR)-2-(1-benzenesulfonyl-2-hydroxy-1-methyl-ethyl)-7-chloro-2,3-dihydro-1H-cyclopenta[b]indole-4-carboxylic acid tert-butyl ester as a white powder.

Workup

  1. customThe reaction was quenched with a saturated NaHCO3 solution
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-5e5381f37ab54543b6582debe1e57995
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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