N-benzyl-N-methyl-1-phenylmethanamine → 3-[Benzyl-(1-phenyl-ethyl)-amino]-3-cyclohexyl-propionic acid tert-butyl ester

HRID 491908Notes

Reaction equation

[CH2:1]([N:8](C)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17]([Li])CCC.[C:22]([O:26][C:27](=[O:36])[CH:28]=[CH:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1)([CH3:25])([CH3:24])[CH3:23]>C1COCC1>[C:22]([O:26][C:27](=[O:36])[CH2:28][CH:29]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:9]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH3:17])[CH:30]1[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]1)([CH3:25])([CH3:23])[CH3:24]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of N-benzyl-(+)-methyl-benzylamine (8.5 mL, 40.4 mmol) in THF (100 mL) was cooled to 0° C., then n-butyl lithium (16 mL, [2.5 M], 40.4 mmol) was added and the resulting mixture stirred for 1 hour. The reaction mixture was cooled to −78° C., then a solution of 3-cyclohexyl-acrylic acid tert-butyl ester (7.71 g, 36.7 mmol) in THF (20 mL) was added dropwise for 30 min and the resulting mixture was stirred an additional 1 hour at −78° C. The reaction was quenched with NH4CT (s), and extracted with EtOAc, the organic layer was dried with MgSO4, filtered and evaporated under reduced pressure to yield a residue. The residue was purified by column chromatography (10%-70% EtOAc/heptane) to yield a residue.

Workup

stirringthe resulting mixture was stirred an additional 1 hour at −78° C
customThe reaction was quenched with NH4CT (s)
extractionextracted with EtOAc
dry with materialthe organic layer was dried with MgSO4
filtrationfiltered
customevaporated under reduced pressure
customto yield a residue
customThe residue was purified by column chromatography (10%-70% EtOAc/heptane)
customto yield a residue

Sources & evidence

ORD record: ord-8782923e3a4648ad96a38f66f191daf4
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07531545B2

Reaction notes

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