Diisobutylaluminumhydride → [1-(2-Trimethylsilanyl-ethanesulfonyl)-1H-indol-5-yl]-methanol

HRID 501925Notes

Reaction equation

[H-].C([Al+]CC(C)C)C(C)C.C([O:13][C:14]([C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[N:21]([S:25]([CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])(=[O:27])=[O:26])[CH:20]=[CH:19]2)=O)C>C1(C)C=CC=CC=1>[CH3:31][Si:30]([CH3:33])([CH3:32])[CH2:29][CH2:28][S:25]([N:21]1[C:22]2[C:18](=[CH:17][C:16]([CH2:14][OH:13])=[CH:24][CH:23]=2)[CH:19]=[CH:20]1)(=[O:27])=[O:26]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of diisobutylaluminum hydride (82.9 mL, 1M in toluene, 82.9 mmol) was added slowly at 0° C. to the solution of 1-(2-trimethylsilanylethanesulfonyl)-1H-indole-5-carboxylic acid ethyl ester (8.81 g, 25.9 mmol) in toluene (200 mL). After it was stirred at 0° C. for 45 min, the reaction was quenched by the addition of methanol (26 mL), pulverized sodium sulfate decahydrate (194 g) and celite (26 mL). The mixture was warmed up to room temperature in 1 h and filtered through a pad of celite. Solvents were removed in vacuo to afford the title compound as a very viscous liquid, which solidified upon cooling. A white solid (8.08 g, 100% yield). 1H-NMR (CDCl3, 500 MHz) δ 7.87 (d, J=8.5 Hz, 1H), 7.62 (s, 1H), 7.44 (d, J=3.7 Hz, 1H), 7.35 (dd, J=8.6, 1.5 Hz, 1H), 6.66 (d, J=3.7 Hz, 1H), 4.79 (s, 2H), 3.18-3.14 (m, 2H), 1.73 (s, 1H), 0.85-0.82 (m, 2H), −0.06 (s, 9H). Mass spec. 312.14 (MH)+.

Workup

customthe reaction was quenched by the addition of methanol (26 mL)
temperatureThe mixture was warmed up to room temperature in 1 h
filtrationfiltered through a pad of celite
customSolvents were removed in vacuo

Sources & evidence

ORD record: ord-9109859e188a46889e283254a433644e
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07772244B2

Reaction notes

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