Sodium sulfate decahydrate → N-Boc-S-trityl-(L)-cysteinal

HRID 964742Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@H:9]([C:31](O)=[O:32])[CH2:10][S:11][C:12]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[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:31]=[O:32])[CH2:10][S:11][C:12]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

Conditions

Temperature: -45 °C

Procedure

The Weinreb amide of N-t-butoxycarbonyl-S-tritylcysteine, prepared above, (406 mg, 0.8 mmol) was dissolved in anhydrous ether (5 ml) and cooled to -45° C. Lithium aluminium hydride (1 ml of a 1N solution in ether, 1 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 (1.25 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 (332 mg, 93%) as a white foam.

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
filtrationhour the solution was filtered through celite
customthe solvent removed under reduced pressure

Sources & evidence

ORD record: ord-239259a167fb432b97505ce0c8aedd67
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05770731

Reaction notes

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