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

HRID 1880923Notes

Reaction equation

[CH:1]1([NH:7][CH2:8][C:9]([OH:16])([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:6][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:7]([CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)[CH2:8][C:9]([OH:16])([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To ethyl 3-(cyclohexylamino)-2-hydroxy-2-methylpropanoate (6.7 g, 29.2 mmol) in 50 ml of acetonitrile at room temperature, was added benzyl bromide (5.2 ml, 43.8 mmol) dropwise, followed by K2CO3 (12 g, 87.6 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 7 g product (75%). [M+H] calc'd for C19H29NO3, 320; found 320.

Workup

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

Sources & evidence

ORD record: ord-6c459cf36c664ed2b4abe7ced064ec4f
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318727B2

Reaction notes

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