Hydrochloric Acid → 3-(4-Chlorophenyl)-3-{7-[(ethylsulfanyl)methyl]-1H-indol-3-yl}propan-1-ol

HRID 561516Notes

Reaction equation

HRID 561516 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[C:23]3[C:18](=[C:19]([CH2:24][S:25][CH2:26][CH3:27])[CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)[CH2:9][C:10](OCC)=[O:11])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:15]2[C:23]3[C:18](=[C:19]([CH2:24][S:25][CH2:26][CH3:27])[CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)[CH2:9][CH2:10][OH:11])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 58392395Ethyl 3-(4-chlorophenyl)-3-{7-[(ethylsulfanyl)methyl]-1H-indol-3-yl}propanoate

Product 1

HCID 583924183-(4-Chlorophenyl)-3-{7-[(ethylsulfanyl)methyl]-1H-indol-3-yl}propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 1.05 g of the compound from Example 33A with a purity of 84% (2.19 mmol) in 20 ml of tetrahydrofuran was added dropwise to 9.1 ml (9.1 mmol) of a 1N solution of lithium aluminum hydride in tetrahydrofuran under argon in 50 ml of tetrahydrofuran at RT. The mixture was stirred at RT for 15 min and then, while cooling in ice, 1N hydrochloric acid was added. The mixture was extracted with dichloromethane, and the organic phase was dried over magnesium sulfate, filtered and concentrated. The crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 0.95 g (94% of theory) of the title compound.

Workup

  1. temperaturewhile cooling in ice
  2. extractionThe mixture was extracted with dichloromethane
  3. dry with materialthe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)

Sources & evidence

ORD record
ord-8d98a62137d24489837ae013c4fd4d4d
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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