Formaldehyde → (+/-)-3-[3-(1-Methyl-1,2,3,6-tetrahydro-4-pyridyl)-1H-indol-5-yl]-2-amino-1-propanol

HRID 128974노트

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HRID 128974 반응식
[CH3:1][O-:2].[Na+].[CH3:4][N:5]1[CH2:10][CH:9]=[C:8]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][CH2:21][N+:22]([O-])=O)[CH:18]=3)[NH:13][CH:12]=2)[CH2:7][CH2:6]1.C=O.O>CN(C=O)C>[CH3:4][N:5]1[CH2:10][CH:9]=[C:8]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][CH:21]([NH2:22])[CH2:1][OH:2])[CH:18]=3)[NH:13][CH:12]=2)[CH2:7][CH2:6]1

참가 물질

6

반응물 4

HCID 712FormaldehydeHCID 962WaterHCID 10942334Sodium MethoxideHCID 15233281HCID 15233281, 화합물

생성물 1

HCID 15233282(+/-)-3-[3-(1-Methyl-1,2,3,6-tetrahydro-4-pyridyl)-1H-indol-5-yl]-2-amino-1-propanol수율 56.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
0 °C

실험 절차

Sodium methoxide (0.30 g) was added to a solution of the product from step (d) (1.5 g) in DMF (15 ml) at 0° C. To the resulting solution was added dropwise a suspension of paraformaldehyde (0.19 g) in DMF (20 ml). The resulting mixture was stirred at 0° C. for 1.5 hours, then poured into water and extracted with ethyl acetate. The combined extracts were washed with water and brine, dried and evaporated in vacuo to give a yellow oil which was eluted through a silica column using DCM/EtOH/NH4OH (50:8:1) as eluant to give the desired product as an off-white solid (0.85 g) which was recrystallised from ethanol.

후처리

  1. additionTo the resulting solution was added dropwise
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with water and brine
  4. customdried
  5. customevaporated in vacuo
  6. customto give a yellow oil which
  7. washwas eluted through a silica column

출처 및 근거

ORD 기록
ord-593ce3846663414d9bc973b96c9f333d
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05466699

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