Tetrabutylammonium Fluoride → Tert-butyl (2r,4r)-4-hydroxy-2-(methoxymethyl)pyrrolidine-1-carboxylate

HRID 908451Notes

Reaction equation

[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([Si](C)(C)[O:24][C@H:25]1[CH2:29][N:28]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C@@H:27]([CH2:37][O:38][CH3:39])[CH2:26]1)(C)(C)C>C1COCC1>[OH:24][C@H:25]1[CH2:29][N:28]([C:30]([O:32][C:33]([CH3:34])([CH3:35])[CH3:36])=[O:31])[C@@H:27]([CH2:37][O:38][CH3:39])[CH2:26]1

Participants

Conditions

Temperature: 20 °C

Procedure

Tetrabutyl ammonium fluoride (21.3 ml) was added to a stirred solution of tert-butyl (2R,4R) 4-(tert-butyl-dimethyl-silyl)oxy-2-(methoxymethyl)pyrrolidine-1-carboxylate (6.68 g) in THF (150 ml). The resulting mixture was stirred at 20° C. for 18 hours. The reaction mixture was evaporated to dryness and the residue was purified by flash chromatography on silica eluting with increasingly polar mixtures of methanol/dichloromethane (0/100-5/95). Fractions containing the desired product were combined and evaporated to give tert-butyl (2R,4R) 4-hydroxy-2-(methoxymethyl)pyrrolidine-1-carboxylate (3.32 g) as a solid. NMR Spectrum: (DMSOd6) 1.44 (9H, s); 1.81-1.86 (1H, m); 2.05 (1H, d); 3.09 (1H, d); 3.43-3.49 (3H, s); 3.52 (3H, m); 3.83 (1H, d); 4.20-4.25 (1H, m); 4.94 (1H, d).

Workup

customThe reaction mixture was evaporated to dryness
customthe residue was purified by flash chromatography on silica eluting
temperaturewith increasingly polar mixtures of methanol/dichloromethane (0/100-5/95)
additionFractions containing the desired product
customevaporated

Sources & evidence

ORD record: ord-d77aca5711024813a1a95e06bbde824d
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017611B2

Reaction notes

Loading…