Water → N-cyclopropyl-6-[(1E)-3-methoxyprop-1-en-1-yl]indan-1-amine

HRID 337647노트

반응식

HRID 337647 반응식
[CH3:1][O:2][CH2:3]/[CH:4]=[CH:5]/[C:6]1[CH:14]=[C:13]2[C:9]([CH2:10][CH2:11][C:12]2=O)=[CH:8][CH:7]=1.[CH:16]1([NH2:19])[CH2:18][CH2:17]1.[BH4-].[Na+].O>CO.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH:16]1([NH:19][CH:12]2[C:13]3[C:9](=[CH:8][CH:7]=[C:6](/[CH:5]=[CH:4]/[CH2:3][O:2][CH3:1])[CH:14]=3)[CH2:10][CH2:11]2)[CH2:18][CH2:17]1

참가 물질

7

반응물 4

HCID 962WaterHCID 69828CyclopropylamineHCID 4311764Sodium borohydrideHCID 670621216-[(1E)-3-Methoxyprop-1-en-1-yl]indan-1-one

생성물 1

HCID 67062179N-cyclopropyl-6-[(1E)-3-methoxyprop-1-en-1-yl]indan-1-amine

시약·촉매·용매 2

HCID 11026Titanium isopropoxide촉매HCID 887Methanol용매

실험 절차

To a solution of 6-[(1E)-3-methoxyprop-1-en-1-yl]indan-1-one (1 eq.) from the previous step in MeOH (2 M) was added cyclopropylamine (2 eq.) and titanium(IV) isopropoxide (1.3 eq.). The solution was stirred at RT for 1 h before sodium borohydride (1 eq.) was added at 0° C. After 30 min, water was added and the mixture was extracted with ethyl acetate. The combined organic extracts were then washed with water and brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product by way of flash chromatography (SiO2, Hex→1:9 (v/v) Hex:EtOAc) afforded the title compound.

후처리

  1. additionwas added at 0° C
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe combined organic extracts were then washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo
  7. customPurification of the crude product by way of flash chromatography (SiO2, Hex→1:9 (v/v) Hex:EtOAc)

출처 및 근거

ORD 기록
ord-235e4f76f48d45bbaa5b34e0e1afff49
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889714B2

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