4-Toluenesulfonyl chloride → (R)-3-tosyloxymethyl-1-methylpiperidine

A solution of (R)-3-hydroxymethyl-1 -methylpiperidine (2.6 g, 20 mmol) in dichloromethane (70 mL) was cooled to 5° C. and tosyl chloride (3.8 g, 20 mmol) was added in portions during 15 minutes. After the addition was complete, the reaction was allowed to warm to room temperature and was stirred for 20 hours. The reaction mixture was then concentrated and the residue partitioned between 10% potassium hydroxide (50 mL) and ether (100 mL). The ether layer was removed and the aqueous phase extracted once again with ether (50 mL). The combined ether layers were dried over magnesium sulfate and concentrated to afford (R)-3-tosyloxymethyl-1 -methylpiperidine as a white solid (2.4 g, 42%), m.p. 74.5-81.0° C.

1. additionAfter the addition
2. concentrationThe reaction mixture was then concentrated
3. customthe residue partitioned between 10% potassium hydroxide (50 mL) and ether (100 mL)
4. customThe ether layer was removed
5. extractionthe aqueous phase extracted once again with ether (50 mL)
6. dry with materialThe combined ether layers were dried over magnesium sulfate
7. concentrationconcentrated

ORD record

ord-1e94244275664d4a8b3a968b22990c44

Source dataset

uspto-grants-2000_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06110937