Methyl iodide → HCID 131731890、化合物

HRID 80843ノート

反応式

HRID 80843 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 131731890HCID 131731890、化合物

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 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).

後処理

  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

出典と根拠

ORDレコード
ord-5cd7a4ebf4ff49aab37b4fd6728e2d66
出典データセット
uspto-grants-2014_09
特許番号
US08846656B2

反応ノート

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