4-Toluenesulfonyl chloride → (S)-tert-Butyl 2-((tosyloxy)methyl)morpholine-4-carboxylate

To a solution of (S)-tert-butyl 2-(hydroxymethyl)morpholine-4-carboxylate (1 g) in dichloromethane (50 mL) was added triethylamine (1.604 mL) and 4-methylbenzene-1-sulfonyl chloride (1.097 g). The mixture was stirred at ambient temperature under nitrogen for 72 hours. The reaction was diluted with methylene chloride (50 mL) and brine (100 mL). The brine layer was extracted with methylene chloride (75 mL). The combined organics were dried over sodium sulfate, filtered and concentrated. The crude material was purified on a silica gel column eluting with a 15-65% ethyl acetate in hexane gradient to provide the title compound.

1. extractionThe brine layer was extracted with methylene chloride (75 mL)
2. dry with materialThe combined organics were dried over sodium sulfate
3. filtrationfiltered
4. concentrationconcentrated
5. customThe crude material was purified on a silica gel column
6. washeluting with a 15-65% ethyl acetate in hexane gradient

ORD record

ord-77865ddb09ff4d03907b26bfc54477de

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09034875B2