Aluminium lithium hydride → (1-Benzyl-3-methoxymethylpyrrolidin-3-yl)methanol

HRID 729442

反応式

HRID 729442 の反応式
[CH2:1]([O:3][C:4]([C:6]1([CH2:18][O:19]C)[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7]1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:11]([N:8]1[CH2:9][CH2:10][C:6]([CH2:18][OH:19])([CH2:4][O:3][CH3:1])[CH2:7]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 690697751-Benzyl-3-methoxymethylpyrrolidine-3-carboxylic acid ethyl ester

生成物 1

HCID 21979083(1-Benzyl-3-methoxymethylpyrrolidin-3-yl)methanol収率 87.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of 1-benzyl-3-methoxymethylpyrrolidine-3-carboxylic acid ethyl ester (Example A18a, 2.30 g, 8.3 mmol) in anhydrous tetrahydrofuran (10 mL) is added dropwise to an ice-cold suspension of lithium aluminum hydride (0.821 g, 22 mmol) in tetrahydrofuran (50 mL). The resulting mixture is stirred at room temperature for 18 hours, cooled and quenched by the sequential dropwise addition of 1N sodium hydroxide and water. The solids are removed by filtration, re-suspended in hot tetrahydrofuran and filtered. The combined filtrates are concentrated in vacuo and the residue is partitioned between dichloromethane and water. The organic extracts are dried over Na2SO4, filtered and concentrated under vacuum to afford the title compound (1.71 g). 1H NMR (200 MHz, CDCl3): δ 7.41-7.17 (m, 5H), 3.84-3.43 (m, 4H), 3.34 (s, 2H), 3.32 (s, 3H), 2.85-2.60 (m, 2H), 2.54-2.14 (m, 31), 1.98-1.50 (m, 2H).

後処理

  1. temperaturecooled
  2. customquenched by the sequential dropwise addition of 1N sodium hydroxide and water
  3. customThe solids are removed by filtration
  4. filtrationfiltered
  5. concentrationThe combined filtrates are concentrated in vacuo
  6. customthe residue is partitioned between dichloromethane and water
  7. dry with materialThe organic extracts are dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-ce522e6f31314400b52507a7db55cbe1
出典データセット
uspto-grants-2009_09
特許番号
US07582627B2

関連ノート

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