Hydrochloric Acid → (S)-2-((R)-3-methoxypyrrolidin-1-yl)propan-1-ol

Hydrogen chloride (2N in Et2O, 1.1 mL, 2.2 mmol) was added to a solution of (R)-3-methoxy-1-((S)-1-(trityloxy)propan-2-yl)pyrrolidine (420 mg, 1.05 mmol) in DCM (5 mL). The reaction mixture was stirred at room temperature for 2 h, diluted with DCM (20 mL), and washed with 2×20 mL saturated aqueous K2CO3. The aqueous layer was back extracted with DCM (10 mL). The combined organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to yield (S)-2-((R)-3-methoxypyrrolidin-1-yl)propan-1-ol as a brown oil (75 mg). 1H NMR (DMSO-d6): 4.31 (t, 1H), 3.82 (m, 1H), 3.47 (m, 1H), 3.18 (m, 1H), 3.15 (s, 3H), 2.77 (dd, 1H), 2.58 (m, 1H), 2.47 (m, 2H), 2.27 (m, 1H), 1.88 (m, 1H), 1.59 (m, 1H), 0.97 (d, 3H).

1. washwashed with 2×20 mL saturated aqueous K2CO3
2. extractionThe aqueous layer was back extracted with DCM (10 mL)
3. dry with materialThe combined organic layer was dried over Na2SO4
4. filtrationfiltered
5. concentrationconcentrated under reduced pressure

ORD record

ord-566b1a05f96747aa9c3850b2b345b6d9

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09187460B2