Methanol → (2S,5S)-tert-butyl 2-(hydroxymethyl)-5-methylpyrrolidine-1-carboxylate

HRID 1412966ノート

反応式

HRID 1412966 の反応式
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH3:13])[CH2:11][CH2:10][C@H:9]1[C:14](O)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].B.CSC.CO>O1CCCC1>[OH:15][CH2:14][C@@H:9]1[CH2:10][CH2:11][C@H:12]([CH3:13])[N:8]1[C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7]

参加物

6

反応物 4

HCID 887MethanolHCID 1068Dimethyl SulfideHCID 6331BoraneHCID 15516206(5S)-1-(tert-Butoxycarbonyl)-5-methyl-L-proline

生成物 1

HCID 12995944(2S,5S)-tert-butyl 2-(hydroxymethyl)-5-methylpyrrolidine-1-carboxylate収率 93%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of (2S,5S)-1-(tert-butoxycarbonyl)-5-methylpyrrolidine-2-carboxylic acid (5.91 g, 25.8 mmol) in tetrahydrofuran at 0° C., was added borane in dimethylsulfide (1.0 M, 3.4 mL, 34 mmol) dropwise. The reaction was stirred for 4 hours at 0° C. then 18 hours at room temperature. The mixture was then cooled to 0° C. and methanol (70 mL) was added dropwise. The reaction was warmed to room temperature and the solvents were removed in vacuo. The residue was taken up in dichloromethane (200 mL) and extracted with saturated sodium bicarbonate. The organic layer was dried with sodium sulfate and the solvent was removed in vacuo to yield (2S,5S)-tert-butyl 2-(hydroxymethyl)-5-methylpyrrolidine-1-carboxylate as a clear oil (5.15 g, 23.9 mmol, 93%) and was used directly in the following step.

後処理

  1. custom18 hours
  2. customat room temperature
  3. temperatureThe mixture was then cooled to 0° C.
  4. temperatureThe reaction was warmed to room temperature
  5. customthe solvents were removed in vacuo
  6. extractionextracted with saturated sodium bicarbonate
  7. dry with materialThe organic layer was dried with sodium sulfate
  8. customthe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-b25173e0754e4d318ccbcc74df78f7be
出典データセット
uspto-grants-2014_12
特許番号
US08921341B2

反応ノート

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