Methyl iodide → 1-(tert-Butyl) 2-methyl 3-hydroxypyrrolidine-1,2-dicarboxylate

HRID 1014915ノート

反応式

HRID 1014915 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([OH:13])[CH:9]1[C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:17]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C.[Cl-].[Na+].O>[CH3:17][O:15][C:14]([CH:9]1[CH:10]([OH:13])[CH2:11][CH2:12][N:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[O:16]

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 140370151-((Tert-butoxy)carbonyl)-3-hydroxypyrrolidine-2-carboxylic acid

生成物 1

HCID 147292541-(tert-Butyl) 2-methyl 3-hydroxypyrrolidine-1,2-dicarboxylate収率 87%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
0 °C

実験手順

A solution containing 3-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (37, 16 g, 71 mmol)1 in DMF (100 mL) was cooled to 0° C. To this solution was added K2CO3 (16 g, 116 mmol) followed by iodomethane (5.4 mL, 87 mmol). The reaction mixture was slowly warmed to ambient temperature over 1 h at which time it became a yellow heterogeneous solution. This mixture was heated at 90° C. for 1 h and then cooled to ambient temperature. The solution was diluted with brine, extracted with diethyl ether, dried over anhydrous Na2SO4, filtered, and concentrated to afford 14.8 g (87%) of 38 as a yellow oil.2 1Hodges, J. A.; Raines, R. T. J. Am. Chem. Soc. 2005, 45, 15923.2Demange, I.; Cluzeau, J.; Menez, A.; Dugave, C. Tetrahedron Lett. 2001, 42, 651.

後処理

  1. temperatureThe reaction mixture was slowly warmed to ambient temperature over 1 h at which time it
  2. temperatureThis mixture was heated at 90° C. for 1 h
  3. temperaturecooled to ambient temperature
  4. extractionextracted with diethyl ether
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-efa32ad14b2c4484a5e9884e74f8d4e6
出典データセット
uspto-grants-2011_07
特許番号
US07985735B2

反応ノート

読み込み中…