Indole → Tryptamine

반응식

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[NH4+:10].[Cl-].C(Cl)(Cl)Cl.Cl[CH:17](Cl)[CH3:18]>>[NH2:10][CH2:17][CH2:18][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1

참가 물질

반응물 4

HCID 798Indole

HCID 6212Chloroform

HCID 63651,1-Dichloroethane2회

HCID 25517Ammonium Chloride

생성물 1

HCID 1150Tryptamine

실험 절차

To a solution of (S)-4b (30 mg) in dichloroethane (1 mL) cooled at −5° C. was dropwise added AgClO4. The resulting mixture was stirred for 15 min at the same temperature and added to a solution of indole (50 mg) in dichloroethane (1 mL) warmed in a reaction flask. The reaction mixture was stirred for 10 h at 50° C. and treated with saturated NH4Cl (mL), and extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to the dryness. The residue was purified by silica gel (60-230 mesh) column chromatography eluted with 10% ethyl acetate in hexanes to afford 5. [α]26D=+190.3 (c=0.1, CHCl3).

후처리

temperaturewarmed in a reaction flask
stirringThe reaction mixture was stirred for 10 h at 50° C.
extractionextracted with CH2Cl2
dry with materialThe combined organic layers were dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo to the dryness
customThe residue was purified by silica gel (60-230 mesh) column chromatography
washeluted with 10% ethyl acetate in hexanes
customto afford 5

출처 및 근거

ORD 기록: ord-6592f99a6e4c437899ca3e16b3a2ce3a
출처 데이터셋: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US09446995B2

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