Tetrahydrofuran → Benzyl 2-(Hydroxymethyl)-1-Indolinecarboxylate

HRID 1168499노트

반응식

HRID 1168499 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[CH2:10][OH:11].C1COCC1.C(=O)(O)[O-].[Na+].[CH2:22]([O:29][C:30](Cl)=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O>[OH:11][CH2:10][CH:2]1[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[N:1]1[C:30]([O:29][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:31]

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 27946642,3-dihydro-1H-indol-2-ylmethanol

생성물 1

HCID 2776402Benzyl 2-(Hydroxymethyl)-1-Indolinecarboxylate수율 99%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A solution containing 2,3-dihydro-1H-indol-2-ylmethanol (Preparation 5, 4.31 g) and THF (60 mL) is added to a flask containing sodium bicarbonate (24.27 g) and water (15 mL). Benzylchloroformate (4.5 mL) is slowly added. Once addition is complete, the mixture is stirred overnight. The crude mixture is filtered and washed with a large amount of CH2Cl2. The filtrate is poured into water and the separated organic phase is washed with 5% HCl and brine. The organic layer is dried (Na2SO4), filtering, and concentrated to give a yellow oil. The crude product is chromatographed eluting with EtOAc/heptane (1/1) to give 8.11 g (99%) of the title compound as a pale colored oil. Physical characteristics: MS (ESI+) m/z 284 (M+H)+.

후처리

  1. additionis added to a flask
  2. additionOnce addition
  3. filtrationThe crude mixture is filtered
  4. washwashed with a large amount of CH2Cl2
  5. additionThe filtrate is poured into water
  6. washthe separated organic phase is washed with 5% HCl and brine
  7. dry with materialThe organic layer is dried (Na2SO4)
  8. filtrationfiltering
  9. concentrationconcentrated
  10. customto give a yellow oil
  11. customThe crude product is chromatographed
  12. washeluting with EtOAc/heptane (1/1)

출처 및 근거

ORD 기록
ord-80570e0bd0a348efb18ebb498324194e
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06624159B2

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