Tetrahydrofuran → HCID 59752197, compound

HRID 750389Notes

Reaction equation

[F-].[CH2:2]([N+](CCCC)(CCCC)CCCC)[CH2:3][CH2:4]C.[Si]([O:26][CH:27]1[C:31]([CH3:33])([CH3:32])[CH2:30][N:29]([C:34]([O-:36])=[O:35])[C:28]1=[O:37])(C(C)(C)C)(C)C.O1[CH2:42][CH2:41][CH2:40][CH2:39]1>>[OH:26][CH:27]1[C:31]([CH3:32])([CH3:33])[CH2:30][N:29]([C:34]([O:36][CH2:39][C:40]2[CH:4]=[CH:3][CH:2]=[CH:42][CH:41]=2)=[O:35])[C:28]1=[O:37]

Participants

Reactant 3

HCID 8028Tetrahydrofuran2×

HCID 2724141Tetrabutylammonium Fluoride

HCID 86601506HCID 86601506, compound

Product 1

HCID 59752197HCID 59752197, compound

Procedure

A solution of tetrabutylammonium fluoride in anhydrous tetrahydrofuran (1.1 mL, 1M, 1.1 mmol) was added to a solution of 3-{[tert-butyl(dimethyl)silyl]oxy}-4,4-dimethyl-2-oxo-1-pyrrolidinecarboxylate (202 mg, 0.54 mmol) in anhydrous tetrahydrofuran (2 mL) under nitrogen. After 45 min, the reaction mixture was subjected directly to column chromatography. Elution with 50% ethyl acetate in hexane afforded benzyl 3-hydroxy-4,4-dimethyl-2-oxo-1-pyrrolidinecarboxylate as an oil that solidified upon standing (133 mg, 94%). 1H NMR (300 MHz, DMSO-d6) δ 7.47-7.36 (m, 1H), 5.88 (d, J=6 Hz, 1H), 5.24 (s, 2H), 3.99 (d, J=6 Hz, 1H), 3.48 (1/2Abq, J=10 Hz, 1H), 3.35 (1/2Abq, J=10 Hz, 1H), 1.11 (s, 3H), 0.89 (s, 3H). ES-LCMS m/z 378 (M+H).

Workup

washElution with 50% ethyl acetate in hexane

Sources & evidence

ORD record: ord-a9d7298474dc4c8081347249d183c4d0
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07402606B2

Reaction notes

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