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

HRID 337647Notes

Reaction equation

HRID 337647 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-235e4f76f48d45bbaa5b34e0e1afff49
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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