Water → 3-(4-Chlorophenyl)-3-cyclopropyl-3-{7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propan-1-ol

HRID 561609Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:27]2[CH2:29][CH2:28]2)([C:15]2[C:23]3[C:18](=[C:19]([CH2:24][S:25][CH3:26])[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-].O.C(#N)C>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH:27]2[CH2:29][CH2:28]2)([C:15]2[C:23]3[C:18](=[C:19]([CH2:24][S:25][CH3:26])[CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)[CH2:9][CH2:10][OH:11])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 62 mg (0.15 mmol) of the compound from Example 105A in 0.5 ml of tetrahydrofuran was added dropwise to 0.51 ml (0.51 mmol) of a 1N solution of lithium aluminum hydride in tetrahydrofuran in 1 ml of tetrahydrofuran at RT under argon. The mixture was stirred at 60° C. for 1 h and then mixed with water and acetonitrile, and the suspension was filtered through kieselguhr. The solvents were removed in a rotary evaporator, and the residue was purified by preparative HPLC (mobile phase: acetonitrile/water gradient). 52 mg (93% of theory) of the title compound were obtained.

Workup

filtrationthe suspension was filtered through kieselguhr
customThe solvents were removed in a rotary evaporator
customthe residue was purified by preparative HPLC (mobile phase: acetonitrile/water gradient)

Sources & evidence

ORD record: ord-b0884d1e30be4ad9a0b74db7f75dd70d
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063234B2

Reaction notes

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