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

HRID 914142
Notes
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Reaction equation

HRID 914142 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 6342
Acetonitrile
Solvent

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-00f69cd42da5432aaad907a0cb1e5701
Source dataset
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08026234B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes