Tert-butyl 3-oxopyrrolidine-1-carboxylate → tert-Butyl 3-hydroxy-3-methylpyrrolidine-1-carboxylate

HRID 1373152Notes

Reaction equation

HRID 1373152 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10](=[O:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:14][Mg]Br>C(OCC)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10]([OH:13])([CH3:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylateHCID 178418573HCID 178418573, compound2×

Product 1

HCID 22951485tert-Butyl 3-hydroxy-3-methylpyrrolidine-1-carboxylateYield 37%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3-Oxo-pyrrolidine-1-carboxylic acid tert-butyl ester [Hofmann, J. Agric. Food Chem., 46, 3902 (1998)] (0.322 g, 1.74 mmol) was dissolved in diethyl ether (5 ml), cooled with an ice bath, and treated with methylmagnesium bromide (3M in ether, 0.64 ml, 1.91 mmol). The reaction was stirred for 1 h then more methylmagnesium bromide added, and the mixture stirred for 63 h. The reaction was quenched with aqueous ammonium chloride and extracted with diethyl ether (×3). The combined organic extracts were dried and evaporated. The residue was purified by flash chromatography, eluting with 0–50% ethyl acetate in petroleum ether, to give the title compound as a sticky off-white solid (0.129 g, 37%); NMR (CDCl3) 1.41 (3H, s), 1.46 (9H, s), 1.61 (1H, s), 1.79–1.92 (2H, m), and 3.17–3.58 (4H, m).

Workup

  1. temperaturecooled with an ice bath
  2. stirringthe mixture stirred for 63 h
  3. customThe reaction was quenched with aqueous ammonium chloride
  4. extractionextracted with diethyl ether (×3)
  5. customThe combined organic extracts were dried
  6. customevaporated
  7. customThe residue was purified by flash chromatography
  8. washeluting with 0–50% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-632aa4c569c740289caf197d8ee4d6eb
Source dataset
uspto-grants-2007_01
Patent number
US07160907B2

Reaction notes

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