Tetrabutylammonium Fluoride → 1-Pyrrolidinecarboxylicacid,3-hydroxy-2-methyl-,1,1-dimethylethylester,(2R,3S)-(9CI)

HRID 1864507Notes

Reaction equation

HRID 1864507 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CC([Si](C)(C)[O:24][C@H:25]1[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C@@H:26]1[CH3:37])(C)C>C1COCC1>[OH:24][C@H:25]1[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C@@H:26]1[CH3:37]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59710338HCID 59710338, compound

Product 1

HCID 450967211-Pyrrolidinecarboxylicacid,3-hydroxy-2-methyl-,1,1-dimethylethylester,(2R,3S)-(9CI)

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutyl ammonium fluoride (16.7 mL, 1N in THF, 16.73 mmol) was added to a solution of 1,1-dimethylethyl(2R,3S)-3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-2-methyl-1-pyrrolidinecarboxylate in THF and stirred for 16 hours at room temperature. The reaction mixture was concentrated under reduced pressure and purified by silica gel column chromatography to yield the title compound (1.55 g, 7.8 mmol). 1H NMR (400 MHz, DMSO-D6) δ ppm 1.0 (m, 3H), 1.4 (s, 9H), 1.6 (m, 1H), 1.9 (m, 1H), 3.3 (m, 2H), 3.5 (m, 1H), 3.8 (m, 1H), 4.9 (s, 1H). ES+=202.15.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-da252548881d4a0283d18f9b1674361b
Source dataset
uspto-grants-2009_12
Patent number
US07625909B2

Reaction notes

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