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

HRID 1373152ノート

反応式

HRID 1373152 の反応式
[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]

参加物

4

反応物 2

HCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylateHCID 178418573HCID 178418573、化合物2 回

生成物 1

HCID 22951485tert-Butyl 3-hydroxy-3-methylpyrrolidine-1-carboxylate収率 37%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-632aa4c569c740289caf197d8ee4d6eb
出典データセット
uspto-grants-2007_01
特許番号
US07160907B2

反応ノート

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