(2R,3R)-3-(tert-Butyldimethylsilanyloxy)-2-hydroxymethylpyrrolidine-1-carboxylic acid tert-butyl ester → (3R)-1-t-Butoxycarbonyl-3-t-butyldimethylsilyloxy-L-proline

HRID 1780279Notes

Reaction equation

CC(C)=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.[C:14]([O:18][C:19]([N:21]1[CH2:27][CH2:26][C@@H:25]([O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])[C@H:22]1[CH2:23][OH:24])=[O:20])([CH3:17])([CH3:16])[CH3:15]>CC(C)=O.O>[C:14]([O:18][C:19]([N:21]1[CH2:27][CH2:26][C@@H:25]([O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:30])[CH3:31])[C@H:22]1[C:23]([OH:3])=[O:24])=[O:20])([CH3:17])([CH3:16])[CH3:15]

Participants

Conditions

Temperature: 0 °C

Procedure

0.7 ml of Jones' reagent (chromium trioxide/4N aqueous sulfuric acid: Bowden, Heibron, Jones & Weedon, J. Chem. Soc., 1946, 39) was added, whilst ice-cooling, to a solution of 245 mg (0.74 mmol) of (3R)-1-t-butoxycarbonyl-3-t-butyldimethylsilyloxy-L-prolinol [prepared as described in step (a) above] in 10 ml of acetone, and the mixture was stirred at 0° C. for 2 hours. At the end of this time, the reaction mixture was diluted with water and extracted with diethyl ether. The extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure, and the residue was triturated with hexane, to give 191 mg of the title compound as colorless crystals, melting at 146°-147° C.

Workup

extractionextracted with diethyl ether
washThe extract was washed with a saturated aqueous solution of sodium chloride
dry with materialdried over anhydrous sodium sulfate
customThe solvent was then removed by distillation under reduced pressure
customthe residue was triturated with hexane

Sources & evidence

ORD record: ord-2c9a389ba50e4b619b8252e2e56b8277
Source dataset: uspto-grants-1997_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05629406

Reaction notes

Loading…