Methyl iodide → HCID 131731890, 화합물

HRID 80843노트

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HRID 80843 반응식
[CH3:1][N:2]([CH3:16])[C@H:3]1[C@H:7]([OH:8])[CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1.[H-].[Na+].I[CH3:20]>C1COCC1>[C:12]([O:11][C:9]([N:5]1[CH2:6][C@@H:7]([O:8][CH3:20])[C@H:3]([N:2]([CH3:16])[CH3:1])[CH2:4]1)=[O:10])([CH3:13])([CH3:15])[CH3:14]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58006925tert-Butyl (3R,4R)-3-(Dimethylamino)-4-hydroxypyrrolidine-1-carboxylate

생성물 1

HCID 131731890HCID 131731890, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a solution of racemic (trans)-tert-butyl 3-(dimethylamino)-4-hydroxypyrrolidine-1-carboxylate (0.96 g, 4.17 mmol) in THF (40 mL) at 0° C. was added NaH (0.25 g, 6.25 mmol, 60% dispersion in mineral oil), and the reaction mixture was stirred at 0° C. for 10 min. Then, iodomethane (0.29 mL, 4.6 mmol) was added dropwise and the resulting mixture was stirred at room temperature for 18 h. The reaction mixture was quenched with sat aq NH4Cl and extracted three times with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated to provide racemic-(trans)-tert-butyl-3-(dimethylamino)-4-methoxypyrrolidine-1-carboxylate. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.84 (br. s., 1 H), 3.46-3.54 (m, 1 H), 3.25 (s, 3 H), 3.12-3.22 (obs m, 3 H), 2.72 (br. s., 1 H), 2.16 (s, 6 H), 1.39 (s, 9 H).

후처리

  1. stirringthe resulting mixture was stirred at room temperature for 18 h
  2. customThe reaction mixture was quenched with sat aq NH4Cl
  3. extractionextracted three times with EtOAc
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-5cd7a4ebf4ff49aab37b4fd6728e2d66
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846656B2

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