Diisobutylaluminum hydride → 3-[4-Fluoro-2-(morpholine-4-sulfonyl)-phenyl]-propionaldehyde

HRID 1971839Notes

Reaction equation

C[O:2][C:3](=O)[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=1[S:13]([N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)(=[O:15])=[O:14].CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[F:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][CH:3]=[O:2])=[C:7]([S:13]([N:16]2[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)(=[O:14])=[O:15])[CH:8]=1

Participants

Conditions

Temperature: -70 °C

Procedure

The solution of the product of example 87 (830 mg, 2.5 mmol) in toluene (5 ml) was cooled down to −70° C. DIBAL-H (1 mol/l in toluene, 3.12 ml) was added dropwise. After completion of addition, the mixture was stirred at −70° C. for one hour. Then the reaction was quenched by adding MeOH (2 ml), after which it was warmed to room temperature. The mixture was dissolved in EA, washed with brine, dried and evaporated under reduced pressure. The residue was purified by column chromatography (PE:EA=3:2) to afford the title compound (355 mg, 47% yield).

Workup

additionAfter completion of addition
customThen the reaction was quenched
additionby adding MeOH (2 ml)
temperatureafter which it was warmed to room temperature
dissolutionThe mixture was dissolved in EA
washwashed with brine
customdried
customevaporated under reduced pressure
customThe residue was purified by column chromatography (PE:EA=3:2)

Sources & evidence

ORD record: ord-30e498ae30a94796ab53fa0e87a32ecb
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431581B2

Reaction notes

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