Methanol → HCID 86745527, compound

HRID 2371492Notes

Reaction equation

[C:1]([CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([F:14])[CH:12]=2)/[C:7](=[CH:15]\[C:16]2[CH:21]=[CH:20][C:19]([S:22][CH3:23])=[CH:18][CH:17]=2)/[C:6]=1[CH3:24])#N.[H-].C([Al+]CC(C)C)C(C)C.C[OH:36]>C1(C)C=CC=CC=1>[F:14][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[CH:15]\[C:16]1[CH:21]=[CH:20][C:19]([S:22][CH3:23])=[CH:18][CH:17]=1)/[C:6]([CH3:24])=[C:5]2[CH2:4][CH2:3][CH:1]=[O:36]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of the nitrile from Step 2 (415 mg, 1.24 mmol) in toluene (4.5 mL) at -78° C. there was added diisobutyl aluminum hydride (1M) in toluene (1.9 mL, 1.9 mmol) and the mixture was stirred at -78° C. for 2 hours; methanol (2 mL) was added and the mixture allowed to warm to room temperature. After partition between ether and water, the residue from evaporation of the organic fraction was chromatographed on silica gel eluting with a 1:2 mixture of ether:hexane to afford the pure title compound as an oil which solidified on standing.

Workup

temperatureto warm to room temperature
customAfter partition between ether and water
customthe residue from evaporation of the organic fraction
customwas chromatographed on silica gel eluting with a 1:2 mixture of ether

Sources & evidence

ORD record: ord-6a4ea032390849789dcb1d167daac7ad
Source dataset: uspto-grants-1992_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05093356

Reaction notes

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