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

HRID 10357

반응식

HRID 10357 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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). 1N 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, 3H), 1.98–1.50 (m, 2H).

후처리

  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

출처 및 근거

ORD 기록
ord-e346e5323871419b8510bb1982209d01
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094780B1

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