Benzyl Bromide → Ethyl 2-((benzyl(cyclopentyl)amino)methyl)-2-hydroxybutanoate

HRID 1880933Notes

Reaction equation

HRID 1880933 reaction equation
[CH:1]1([NH:6][CH2:7][C:8]([OH:16])([CH2:14][CH3:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>C(#N)C>[CH2:17]([N:6]([CH2:7][C:8]([OH:16])([CH2:14][CH3:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 57955553Ethyl 2-((cyclopentylamino)methyl)-2-hydroxybutanoate

Product 1

HCID 57955651Ethyl 2-((benzyl(cyclopentyl)amino)methyl)-2-hydroxybutanoateYield 77%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To ethyl 2-((cyclopentylamino)methyl)-2-hydroxybutanoate (2.7 g, 12 mmol) in 50 ml of acetonitrile at room temperature, was added benzyl bromide (2.1 ml, 18 mmol) dropwise, followed by K2CO3 (5 g, 35 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 4:1) to give 2.9 g product (77%). [M+H] calc'd for C19H29NO3, 320; found 320.

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 4:1)

Sources & evidence

ORD record
ord-8bda5367c9aa4349ad4fe0ed1fca0d97
Source dataset
uspto-grants-2012_11
Patent number
US08318727B2

Reaction notes

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