Diisobutylaluminum hydride → 2-[1-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl) cyclopropyl]ethanol

HRID 1683976Notes

Reaction equation

[Br:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([C:18]3([CH2:21][C:22](OC)=[O:23])[CH2:20][CH2:19]3)=[C:8]2[CH3:26])=[CH:4][CH:3]=1.CC(C[AlH]CC(C)C)C>C1COCC1>[Br:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([C:18]3([CH2:21][CH2:22][OH:23])[CH2:19][CH2:20]3)=[C:8]2[CH3:26])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a -78° C. solution of ester from Step 7 (442 mg, 1 mmol) in 5 mL THF was added DIBAH (1.5M in toluene, 2 mL, 3 mmol), and the mixture was stirred for 2 hours with slow warming to 0° C. The reaction mixture was partitioned between 1N HCl and ethyl acetate. The organic layer was washed with brine, dried over MgSO4 and evaporated. The residue was filtered through a plug of silica gel to give 319 mg of the title compound which was used without further purification.

Workup

customThe reaction mixture was partitioned between 1N HCl and ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over MgSO4
customevaporated
filtrationThe residue was filtered through a plug of silica gel

Sources & evidence

ORD record: ord-269b11486e864ab3bc0d1163300f15f4
Source dataset: uspto-grants-1997_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05639780

Reaction notes

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