Triethylamine → (2-hydroxy-ethyl)-(1H-indol-7-ylmethyl)-carbamic acid benzyl ester

HRID 2234909노트

반응식

HRID 2234909 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[CH2:10][NH:11][CH2:12][CH2:13][OH:14])[CH:3]=[CH:2]1.C(N(CC)CC)C.Cl[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24]>ClCCCl>[CH2:26]([O:25][C:23](=[O:24])[N:11]([CH2:12][CH2:13][OH:14])[CH2:10][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[NH:1][CH:2]=[CH:3]2)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 219500502-[(1H-Indol-7-ylmethyl)amino]-ethan-1-ol

생성물 1

HCID 67017088(2-hydroxy-ethyl)-(1H-indol-7-ylmethyl)-carbamic acid benzyl ester수율 52%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

To a solution of 2-[(1H-indol-7-ylmethyl)-amino]-ethanol (4.4 g) in 1,2-dichloroethane (40 mL) was added triethylamine (4.85 mL, 34.6 mmol) followed by benzyl chloroformate (3.57 mL, 25.34 mmol). The mixture was allowed to stir at room temperature for 2 hours. The mixture was quenched by addition of water (20 mL), and 1.0 M sodium hydroxide (10 mL). The organic layer was separated and the aqueous layer extracted with 1,2-dichloroethane (20 mL). The combined organic extracts were washed with 1.0 M hydrochloric acid (20 mL), water (20 mL), dried over anhydrous sodium sulfate and evaporated to dryness. The residue was purified by silica gel chromatography, eluting with 20% ethyl acetate in hexanes to 40% ethyl acetate in hexanes to afford (2-hydroxy-ethyl)-(1H-indol-7-ylmethyl)-carbamic acid benzyl ester (2.79 g, 52% combined yield for two steps) as a colorless oil. 1H NMR (CDCl3) 400 MHz δ: 9.97 (br s, 1H), 7.75-6.9 (m, 8H), 6.54 (br s, 1H), 5.21 (s, 2H), 4.9-4.6 (m, 3H), 3.85-3.57 (m, 2H), 3.55-3.23 (m, 3H); LCMS M+H=325.

후처리

  1. customThe mixture was quenched by addition of water (20 mL), and 1.0 M sodium hydroxide (10 mL)
  2. customThe organic layer was separated
  3. extractionthe aqueous layer extracted with 1,2-dichloroethane (20 mL)
  4. washThe combined organic extracts were washed with 1.0 M hydrochloric acid (20 mL), water (20 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated to dryness
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with 20% ethyl acetate in hexanes to 40% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-4dbee05761af4287836e2d49d527928c
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07713969B2

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