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

HRID 1412966노트

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HRID 1412966 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b25173e0754e4d318ccbcc74df78f7be
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921341B2

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