HCID 13600823, compound → HCID 60208175, compound

HRID 2185686Notes

Reaction equation

HRID 2185686 reaction equation
[CH3:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]1[C:11]([O:13]C)=O>C(N)CCC>[CH2:3]([NH:4][C:11]([CH:3]1[CH:2]([CH3:1])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4]1)=[O:13])[CH2:2][CH2:10][CH3:9]

Participants

3

Reactant 1

HCID 13600823HCID 13600823, compound

Product 1

HCID 60208175HCID 60208175, compound

Reagents, catalysts & solvents 1

HCID 8007ButylamineSolvent

Procedure

Methyl 3-(R/S)-methylindoline-2(R/S)-carboxylate (3.60 g, 18.8 mmol) was dissolved in butylamine (100 ml) under nitrogen and the solution was then stirred at reflux for 3 hours. After cooling the mixture, the remaining butylamine was removed under vacuum. The crude product was purified by chromatography on a column of silica gel, using a 7/3 and then a 5/5 petroleum ether/ethyl acetate mixture as eluent. Two main fractions were collected. The first was a white solid which is the trans isomer.

Workup

  1. temperatureat reflux for 3 hours
  2. temperatureAfter cooling the mixture
  3. customthe remaining butylamine was removed under vacuum
  4. customThe crude product was purified by chromatography on a column of silica gel
  5. customTwo main fractions were collected

Sources & evidence

ORD record
ord-1058d287f3844892b66f91fa1bd8c544
Source dataset
uspto-grants-2002_06
Patent number
US06403561B1

Reaction notes

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