Benzyl Bromide → Ethyl 3-(benzyl(cyclopentyl)amino)-2-hydroxy-2-methylpropanoate

HRID 1880913Notes

Reaction equation

HRID 1880913 reaction equation
[CH:1]1([NH:6][CH2:7][C:8]([OH:15])([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>C(#N)C>[CH2:16]([N:6]([CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5]1)[CH2:7][C:8]([OH:15])([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 57955584Ethyl 3-(cyclopentylamino)-2-hydroxy-2-methylpropanoate

Product 1

HCID 57955626Ethyl 3-(benzyl(cyclopentyl)amino)-2-hydroxy-2-methylpropanoateYield 77%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To ethyl 3-(cyclopentylamino)-2-hydroxy-2-methylpropanoate (3.9 g, 18 mmol) in 50 ml of acetonitrile at room temperature, was added benzyl bromide (3.2 ml, 27.2 mmol) dropwise, followed by K2CO3 (7.5 g, 54.3 mmol). The reaction mixture was heated at 80° C. for 18 h. It was then diluted to EtOAc, washed by brine and water. Organic extract dried and concentrated to a residue, which was purified on silica gel column chromatographically (Hex/EtOAc=100:1 to 10:1) to give 4.2 g product (77%). [M+H] calc'd for C18H27NO3, 306; found 306.

Workup

  1. washwashed by brine and water
  2. extractionOrganic extract
  3. customdried
  4. concentrationconcentrated to a residue, which
  5. customwas purified on silica gel column chromatographically (Hex/EtOAc=100:1 to 10:1)

Sources & evidence

ORD record
ord-6df4d33aff5a4f7993c377868b0cbf96
Source dataset
uspto-grants-2012_11
Patent number
US08318727B2

Reaction notes

Loading…