Water → tert-butyl N-((2R)-1-oxopropan-2-yl)carbamate

Water (2.57 ml, 143 mmol) was added dropwise to a mixture of (R)-tert-butyl (1-hydroxypropan-2-yl)carbamate (17.85 g, 102 mmol) and Dess-Martin Periodinane (60.5 g, 143 mmol) in anhydrous DCM (500 ml) at rt under a nitrogen atmosphere. The reaction was allowed to stir at rt overnight before diluting with diethyl ether and filtering. The filtrate was evaporated in vacuo and the residue diluted with diethyl ether. The organic was then washed with a 1:1 mixture of 10% aq sodium thiosulfate solution: sat. sodium bicarbonate solution, followed by brine and water. The aqueous phase was then back extracted with one portion of diethyl ether, the combined organics were then dried (MgSO4) and evaporated in vacuo to give (R)-tert-butyl (1-oxopropan-2-yl)carbamate (15 g, 87 mmol, 85% yield) as a white solid.

1. filtrationfiltering
2. customThe filtrate was evaporated in vacuo
3. additionthe residue diluted with diethyl ether
4. washThe organic was then washed with a 1:1 mixture of 10% aq sodium thiosulfate solution
5. extractionThe aqueous phase was then back extracted with one portion of diethyl ether
6. dry with materialthe combined organics were then dried (MgSO4)
7. customevaporated in vacuo

ORD record

ord-cc5a49085c76434e94cf9989d597aa21

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09221826B2