Tetrabutylammonium Fluoride → tert-butyl (2S,4R)-4-hydroxy-2-(propan-2-yl)pyrrolidine-1-carboxylate

HRID 81128Notes

Reaction equation

HRID 81128 reaction equation
[Si]([O:8][C@H:9]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@H:11]([CH:21]([CH3:23])[CH3:22])[CH2:10]1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>O1CCCC1>[OH:8][C@H:9]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:15])[C@H:11]([CH:21]([CH3:23])[CH3:22])[CH2:10]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86724490tert-butyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-(propan-2-yl)pyrrolidine-1-carboxylate

Product 1

HCID 60054987tert-butyl (2S,4R)-4-hydroxy-2-(propan-2-yl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of tert-butyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-(propan-2-yl)pyrrolidine-1-carboxylate (50 g) dissolved in tetrahydrofuran was added tetra-N-butylammonium fluoride (95 g) dissolved in tetrahydrofuran (250 mL) at 0° C. The mixture was stirred for 16 h at room temperature and then quenched with water (100 mL). The solution was washed with hydrochloric acid (6 N), extracted with ethyl acetate (3×100 mL), dried over magnesium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography (2/1 petroleum ether/ethyl acetate) to afford tert-butyl (2S,4R)-4-hydroxy-2-(propan-2-yl)pyrrolidine-1-carboxylate.

Workup

  1. customquenched with water (100 mL)
  2. washThe solution was washed with hydrochloric acid (6 N)
  3. extractionextracted with ethyl acetate (3×100 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (2/1 petroleum ether/ethyl acetate)

Sources & evidence

ORD record
ord-79554687da2e4887ae244ed747aa4f9f
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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