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

HRID 1029637Notes

Reaction equation

HRID 1029637 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]([CH2:21][O:22][CH3:23])[CH2:10]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:17]([O:16][C:14]([N:12]1[CH2:13][CH:9]([OH:8])[CH2:10][CH:11]1[CH2:21][O:22][CH3:23])=[O:15])([CH3:20])([CH3:19])[CH3:18]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 15117246(2S,4R)-4-(tert-butyldimethylsilyloxy)-1-(tert-butoxycarbonyl)-2-methoxymethylpyrrolidine

Product 1

HCID 19900165Tert-butyl 4-hydroxy-2-(methoxymethyl)pyrrolidine-1-carboxylateYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (2S,4R)-4-(tert-butyldimethylsilyloxy)-1-(tert-butoxycarbonyl)-2-methoxymethylpyrrolidine (4.48 g) and tetrabutylammonium fluoride (1 Mol tetrahydrofuran solution, 13 ml) in tetrahydrofuran (45 ml) was stirred at 0° C. for eight hours. The reaction mixture was extracted with ethyl acetate, and the organic layer was separated, washed with brine, dried over magnesium sulfate. Evaporation of the solvent gave an oil, which was chromatographed on silica gel (300 ml) eluting with a mixture of hexane and ethyl acetate (1:2, V/V) to give (2S,4R)-1-(tert-butoxycarbonyl-4-hydroxy-2-methoxymethylpyrrolidine (2.82 g).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. customthe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvent
  6. customgave an oil, which
  7. customwas chromatographed on silica gel (300 ml)
  8. washeluting with a mixture of hexane and ethyl acetate (1:2, V/V)

Sources & evidence

ORD record
ord-4c5ed35b2d8c4313bcc6244d48ded402
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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