Water → 3-(2,3-Dihydro-1,4-benzodioxin-6-yl)-3-{7-[(methylsulfanyl)methyl]-1H-indol-3-yl}butan-1-ol

HRID 561610Notes

Reaction equation

[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([C:19]3[C:27]4[C:22](=[C:23]([CH2:28][S:29][CH3:30])[CH:24]=[CH:25][CH:26]=4)[NH:21][CH:20]=3)([CH3:18])[CH2:12][C:13](OCC)=[O:14])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.C(#N)C>O1CCCC1>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([C:19]3[C:27]4[C:22](=[C:23]([CH2:28][S:29][CH3:30])[CH:24]=[CH:25][CH:26]=4)[NH:21][CH:20]=3)([CH3:18])[CH2:12][CH2:13][OH:14])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 625 mg (1.47 mmol) of the compound from Example 106A in 3 ml of tetrahydrofuran was added dropwise to 5.14 ml (5.14 mmol) of a 1N solution of lithium aluminum hydride in tetrahydrofuran in 6 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). 491 mg (87% 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-652cbf2374eb440c98b5bbc5c7c61a58
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063234B2

Reaction notes

Loading…