Acetic Acid → N-Benzyl-3-(5-fluoro-1H-indol-3-yl)-cyclopentylamine

HRID 1824007노트

반응식

HRID 1824007 반응식
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]1[CH2:15][CH2:14][C:13](=O)[CH2:12]1.[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>[OH-].[Na+]>[CH2:17]([NH:24][CH:13]1[CH2:14][CH2:15][CH:11]([C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=3)[NH:7][CH:6]=2)[CH2:12]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 7504BenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 221394665-Fluoro-3-(3-oxycyclopentyl)indole

생성물 1

HCID 22149137N-Benzyl-3-(5-fluoro-1H-indol-3-yl)-cyclopentylamine수율 105.5%

시약·촉매·용매 1

HCID 14798Sodium Hydroxide용매

실험 절차

A mixture 3-(5-fluoro-1H-indol-3-yl)-cyclopentanone (1.0 g, 4.61 mmol), benzylamine (0.54 g, 5.05 mmol) and glacial acetic acid (0.7 mL, 1.08 mmol) were stirred at room temperature for 30 min. Sodium triacetoxyborohydride (1.5 g, 7.11 mmole) was added portionwise over a 10 min period. The reaction was stirred at room temperature for 24 hours. The reaction mixture was poured into 1 N aqueous NaOH (80 mL) and extracted with ethyl acetate (3×100 mL). The combined organic layers were washed with H2O (100 mL) and brine (100 mL), then were dried over anhydrous sodium sulfate, filtered and concentrated to give 1.5 g of a thick yellow oil. Flash chromatography on silica gel (7% 2 M NH3 in methanol/ethyl acetate) afforded 0.5 g of the cis isomer (first eluting) and 0.5 g of the trans isomer.

후처리

  1. extractionextracted with ethyl acetate (3×100 mL)
  2. washThe combined organic layers were washed with H2O (100 mL) and brine (100 mL)
  3. dry with materialwere dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-654ce13acd30451bbaaad56ceb83e4f2
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07041697B2

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