(9-Benzyl-1,8-diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid → HCID 11349041, 화합물

HRID 2249556노트

반응식

HRID 2249556 반응식
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[CH2:17][CH3:18])[C:10]2[CH2:19][CH2:20][O:21][C:22]([CH2:25][C:26](O)=[O:27])([CH2:23][CH3:24])[C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCCC1>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[CH2:17][CH3:18])[C:10]2[CH2:19][CH2:20][O:21][C:22]([CH2:25][CH2:26][OH:27])([CH2:23][CH3:24])[C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

3

반응물 1

HCID 69196678(9-Benzyl-1,8-diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid

생성물 1

HCID 11349041HCID 11349041, 화합물수율 74%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
90 °C

실험 절차

To a solution of (9-benzyl-1,8-diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid (0.45 g, 1.2 mmol) in tetrahydrofuran at room temperature was added 1.0 M solution of borane-tetrahydrofuran complex in tetrahydrofuran and it was stirred at 90° C. for 4 hours. The mixture was quenched with 5% HCl solution and stirred at room temperature for 20 minutes. It was extracted with ethyl acetate and washed with saturated sodium bicarbonate. The extracts were dried over magnesium sulfate and evaporated to dryness. Flash chromatography on silica gel provided 0.321 g (74%) of the title compound as a solid. 1H NMR (500 MHz, CDCl3) δ 7.17 (m, 3H), 6.94 (d, 1H), 6.84 (m, 2H), 6.70 (t, 1H), 6.56 (d, 1H), 3.87 (m, 1H), 3.79 (m, 1H), 3.68 (dt, 1H), 3.64 (br, 1H), 3.41 (td, 1H), 2.93 (q, 2H), 2.43 (q, 2H), 2.04 (m, 1H), 1.93 (dt, 1H), 1.86 (m, 1H), 1.77 (m, 1H), 1.49 (m, 1H), 1.38 (m, 1H), 1.17 (t, 3H), 0.70 (t, 3H)

후처리

  1. customThe mixture was quenched with 5% HCl solution
  2. stirringstirred at room temperature for 20 minutes
  3. extractionIt was extracted with ethyl acetate
  4. washwashed with saturated sodium bicarbonate
  5. dry with materialThe extracts were dried over magnesium sulfate
  6. customevaporated to dryness

출처 및 근거

ORD 기록
ord-3e9256beb3564209abe653bf75c0e1a3
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07314886B2

반응 노트

불러오는 중…