Aluminium lithium hydride → HCID 58986338, compound

HRID 420804Notes

Reaction equation

[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][O:19]3)=[CH:14][CH:15]=2)[C:10]([C:24](OCC)=[O:25])=[C:9]1[CH:29]([CH3:31])[CH3:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][O:19]3)=[CH:14][CH:15]=2)[C:10]([CH2:24][OH:25])=[C:9]1[CH:29]([CH3:31])[CH3:30])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To −78° C. solution of 1-benzyl-2-isopropyl-5-(tetrahydropyran-2-yloxy)-1H-indole-3-carboxylic acid, ethyl ester (Compound 11, 2.11 g, 5 mmol) in THF (30 mL) was added a 1 M solution of LiAlH4 in THF (9 mL, 9 mmol) dropwise over 5 minutes. The mixture was gradually warmed to 0° C. over 4 h. The reaction was cooled to −78° C. and quenched by adding EtOAc (5 mL) and saturated aqueous Na2SO4 (9 mL). The solution was warmed to room temperature and stirred for 20 minutes. The resulting precipitate was filtered off, and the organic layer was dried (Na2SO4). The solvent was removed under vacuum to obtain (1-benzyl-2-isopropyl-5-(tetrahydropyran-2-yloxy)-1H-indol-3-yl)methanol (Compound 12) as a white solid.

Workup

temperatureThe reaction was cooled to −78° C.
customquenched
additionby adding EtOAc (5 mL) and saturated aqueous Na2SO4 (9 mL)
temperatureThe solution was warmed to room temperature
filtrationThe resulting precipitate was filtered off
dry with materialthe organic layer was dried (Na2SO4)
customThe solvent was removed under vacuum

Sources & evidence

ORD record: ord-bf64b1a89a594c02902294fc5fd58d1f
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08097644B2

Reaction notes

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