Diisobutylaluminumhydride → (3S)-3-(triethylsilyloxy)-3-(6-quinolyl)propanal

HRID 2296843Notes

Reaction equation

[CH2:1]([Si:3]([CH2:35][CH3:36])([CH2:33][CH3:34])[O:4][CH:5]([C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[N:29]=[CH:28][CH:27]=[CH:26]2)[CH2:6][C:7](N1[C@@H]2CC3C(C)(C)C2(CC3)CS1(=O)=O)=[O:8])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl.CCCCCC>[CH2:35]([Si:3]([CH2:1][CH3:2])([CH2:33][CH3:34])[O:4][C@H:5]([C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[N:29]=[CH:28][CH:27]=[CH:26]2)[CH2:6][CH:7]=[O:8])[CH3:36]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of (2R)-N-[3-(triethylsilyloxy)-3-(6-quinolyl)-propionyl]bornane-10,2-sultam (52.8 gm) in 1000 mL of CH2Cl2 is cooled to −78° C, and a 1.0 M solution of diisobutylaluminum hydride in hexane is added dropwise so as to keep the reaction temperature below −65° C. The mixture is stirred for an additional 6 hours at −78° C., then is quenched by addition of sat. aq. NH4Cl and allowed to warm to ambient temperature. The mixture is washed with brine, and the organic phase is dried over MgSO4, filtered, and evaporated. The product is purified by silica gel chromatography.

Workup

customthe reaction temperature below −65° C
customis quenched by addition of sat. aq. NH4Cl
temperatureto warm to ambient temperature
washThe mixture is washed with brine
dry with materialthe organic phase is dried over MgSO4
filtrationfiltered
customevaporated
customThe product is purified by silica gel chromatography

Sources & evidence

ORD record: ord-f017f5741a694401b80a15a5c10c266b
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06489314B1

Reaction notes

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