Cyclopropylamine → HCID 137329929, compound

HRID 2428116Notes

Reaction equation

HRID 2428116 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[C:5]([SiH2:9][O:10][C:11]([CH3:27])([CH3:26])[C:12]1[CH:13]=[C:14]([CH2:19][CH2:20]OS(C)(=O)=O)[CH:15]=[CH:16][C:17]=1[Cl:18])([CH3:8])([CH3:7])[CH3:6]>CCO>[C:5]([SiH2:9][O:10][C:11]([CH3:26])([CH3:27])[C:12]1[CH:13]=[C:14]([CH2:19][CH2:20][NH:4][CH:1]2[CH2:3][CH2:2]2)[CH:15]=[CH:16][C:17]=1[Cl:18])([CH3:8])([CH3:7])[CH3:6]

Participants

4

Reactant 2

HCID 69828Cyclopropylamine2×HCID 137329927HCID 137329927, compound

Product 1

HCID 137329929HCID 137329929, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Cyclopropylamine (1.14 mL, 16.3 mmol) was added to a sol. of methanesulfonic acid 2-[3-(tert-butyl-dimethyl-silanyloxymethyl)-4-chloro-phenyl]-ethyl ester (1.76 g, 4.65 mmol) in EtOH (46 mL). The mixture was heated to reflux for 2 h, and cyclopropylamine (0.57 mL, 8.2 mmol) was added again. The mixture was heated to reflux overnight, and was allowed to cool to rt. The solvents were removed under reduced pressure, and the residue was purified by FC (EtOAc/heptane 50:50→7M NH3/MeOH) to yield the title compound (865 mg, 68%). LC-MS: tR=0.92 min; ES+: 340.39.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 h
  3. temperatureThe mixture was heated
  4. temperatureto reflux overnight
  5. customThe solvents were removed under reduced pressure
  6. customthe residue was purified by FC (EtOAc/heptane 50:50→7M NH3/MeOH)

Sources & evidence

ORD record
ord-37d1b6eb933d46ffade8eb1e99082961
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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