Diisobutylaluminum hydride → HCID 12073621, compound

HRID 561761Notes

Reaction equation

[Si:1]([O:18][CH2:19][C@@H:20]1[C@@H:27]2[C@@H:23]([O:24][C:25](=[O:28])[CH2:26]2)[CH2:22][C@@H:21]1[F:29])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C[AlH]CC(C)C)C>C1COCC1>[Si:1]([O:18][CH2:19][C@@H:20]1[C@@H:27]2[C@@H:23]([O:24][CH:25]([OH:28])[CH2:26]2)[CH2:22][C@@H:21]1[F:29])([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a stirring solution consisting of (3aR,4S,5S,6aS)-4-((tert-butyldiphenylsilyloxy)methyl)-5-fluorohexahydro-2H-cyclopenta[b]furan-2-one (prepared in Step A, 26.6 g, 64.6 mmol) in anhydrous THF (1 L) cooled to −78° C. was added DIBAL-H (1 M solution in THF; 200 mL) dropwise. The reaction mixture was stirred at −78° C. and reaction progress was monitored by TLC. After 2 hours, the reaction mixture was quenched by the addition of 2:1 THF-water at −78° C. and the reaction mixture was allowed to warm to room temperature with stirring until precipitated aluminum salts settled out of solution. The aluminum salts were removed by filtration through a sintered glass fritted filter funnel and the filtrate was evaporated to dryness to afford the title intermediate (26 g) The crude intermediate was carried on with no further purification.

Workup

customreaction progress
customthe reaction mixture was quenched by the addition of 2:1 THF-water at −78° C.
temperatureto warm to room temperature
stirringwith stirring
customuntil precipitated aluminum salts
customThe aluminum salts were removed by filtration through a sintered glass fritted filter funnel
customthe filtrate was evaporated to dryness

Sources & evidence

ORD record: ord-aca8172c78984872812a2727d02e88ad
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063240B2

Reaction notes

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