Sodium sulfate decahydrate → 1,1-Dimethylethyl N-((1S,2S)-1-formyl-2-methylbutyl)carbamate

HRID 964740Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14](O)=[O:15])[C@H:10]([CH2:12][CH3:13])[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>CCOCC>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH:14]=[O:15])[C@H:10]([CH2:12][CH3:13])[CH3:11])=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

Conditions

Temperature: -45 °C

Procedure

The Weinreb amide of N-t-butoxycarbonylisoleucine, prepared above, (1.98 g, 7.2 mmol) was dissolved in anhydrous ether (10 ml) and cooled to -45° C. Lithium aluminium hydride (10 ml of a 1N solution in ether, 10 mmol) was then added keeping the temperature below -35° C., after addition the solution was then allowed to warm to 5° C. The solution was then cooled to -45° C. and sodium sulfate decahydrate (5.00 g) added and the cooling bath removed. After 1 hour the solution was filtered through celite and the solvent removed under reduced pressure to yield the aldehyde (1.47 g, 95%) as a colourless oil, which was immediately used in the next reaction as it racemises at room temperature.

Workup

customthe temperature below -35° C.
additionafter addition the solution
temperatureto warm to 5° C
temperatureThe solution was then cooled to -45° C.
customthe cooling bath removed
filtrationAfter 1 hour the solution was filtered through celite
customthe solvent removed under reduced pressure

Sources & evidence

ORD record: ord-99bb6b41450641c8bcd2d71a7db8d0c5
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05770731

Reaction notes

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