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-Eintrag

ord-435583a5ceb14ddb9c313e5166b076e0

Quelldatensatz

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09174982B2