Ammonium formate → Ethyl 2-(2-hydroxy-6,7,8,9-tetrahydropyrido[1,2-a]indol-9-yl)acetate

HRID 515741

반응식

HRID 515741 반응식
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]1[CH2:18][CH2:19][CH2:20][C:21](=[CH:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:13]1=[CH:12]2)C1C=CC=CC=1.C([O-])=O.[NH4+]>C1COCC1.CO.[OH-].[Pd+2].[OH-]>[OH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]1[CH2:18][CH2:19][CH2:20][CH:21]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:13]1=[CH:12]2

참가 물질

5

반응물 2

HCID 2723923Ammonium formateHCID 67249894Ethyl 2-(2-(Benzyloxy)-7,8-dihydropyrido[1,2-a]indol-9(6H)-ylidene)acetate

생성물 1

HCID 67249257Ethyl 2-(2-hydroxy-6,7,8,9-tetrahydropyrido[1,2-a]indol-9-yl)acetate수율 87.4%

시약·촉매·용매 2

HCID 9942167Palladium hydroxide촉매HCID 21899815MeOH tetrahydrofuran용매

실험 절차

Ethyl 2-(2-(benzyloxy)-7,8-dihydropyrido[1,2-a]indol-9(6H)-ylidene)acetate (608 mg, 1.682 mmol) was dissolved in THF/MeOH (1:1) (4 mL). Ammonium formate (648 mg, 10.28 mmol) and palladium hydroxide (20 wt % Pd on carbon) (60 mg) was added under nitrogen protection. The reaction was heated at reflux for 5 h. The solid was filtered. The filtrate was concentrated, dissolved in ethyl acetate, washed with water, dried over anhydrous Na2SO4, and concentrated. The residue was purified by silica gel column chromatography to give the title compound (402 mg) as colorless oil. LCMS m/z=274.3 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 1.32 (t, J=7.1 Hz, 3H), 1.50-1.61 (m, 1H), 1.98-2.08 (m, 1H), 2.08-2.22 (m, 2H), 2.55 (dd, J=15.6 and 8.7 Hz, 1H), 2.94 (dd, J=15.6, 5.5 Hz, 1H), 3.44-3.52 (m, 1H), 3.80-3.88 (m, 1H), 4.07-4.13 (m, 1H), 4.24 (q, J=7.1 Hz, 2H), 4.95 (s, 1H), 6.12 (s, 1H), 6.74 (dd, J=8.6, 2.4 Hz, 1H), 6.95 (d, J=2.4 Hz, 1H), 7.10 (d, J=8.6 Hz, 1H).

후처리

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 5 h
  3. filtrationThe solid was filtered
  4. concentrationThe filtrate was concentrated
  5. dissolutiondissolved in ethyl acetate
  6. washwashed with water
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-8b7afd97a8344624b935314f7c8c36c9
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108969B2

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