Triethylamine → HCID 86714763, compound

HRID 2171886Notes

Reaction equation

HRID 2171886 reaction equation
[CH2:1]([NH:8][OH:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:17][C:18]1([CH:22]=[CH:23][C:24](OC)=[O:25])[CH2:21][CH2:20][CH2:19]1>ClCCl.O>[CH2:1]([N:8]1[CH:22]([C:18]2([CH3:17])[CH2:21][CH2:20][CH2:19]2)[CH2:23][C:24](=[O:25])[O:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2794173BenzylhydroxylamineHCID 77821784HCID 77821784, compound

Product 1

HCID 86714763HCID 86714763, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
50 °C

Procedure

N-benzylhydroxylamine (hydrochloric acid) (0.28 g, 1.80 mmol) and triethylamine (0.28 mL, 2.00 mmol) were added to a solution of methyl 3-(1-methylcyclobutyl)acrylate, 114a, (0.26 g, 1.50 mmol) in dichloromethane (9.5 mL). The reaction mixture was stirred at 50° C. overnight. The reaction mixture was cooled to room temperature and the mixture was diluted with dichloromethane and water. The layers were separated with a phase separator and the aqueous layer was washed with dichloromethane. The organic layers were combined and the volatiles removed under reduced pressure. The residue was purified on silica gel (EtOAc/Hexanes) to afford the desired product as a racemic mixture: LCMS Gradient 10-90%, 0.1% formic acid, 5 minutes, C18/ACN, RT=1.47 minutes (M+H) 246.10.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe layers were separated with a phase separator
  3. washthe aqueous layer was washed with dichloromethane
  4. customthe volatiles removed under reduced pressure
  5. customThe residue was purified on silica gel (EtOAc/Hexanes)

Sources & evidence

ORD record
ord-93b0b6e288584ab9a8017338009057dd
Source dataset
uspto-grants-2015_06
Patent number
US09051319B2

Reaction notes

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