Methyl Acrylate → HCID 178500792, compound

HRID 2404137Notes

Reaction equation

HRID 2404137 reaction equation
[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([C:22]([NH2:25])([CH3:24])[CH3:23])[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[C:26]([O:30][CH3:31])(=[O:29])[CH:27]=[CH2:28]>CO>[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([C:22]([NH:25][CH2:28][CH2:27][C:26]([O:30][CH3:31])=[O:29])([CH3:24])[CH3:23])[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 7294Methyl AcrylateHCID 178456728HCID 178456728, compound

Product 1

HCID 178500792HCID 178500792, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(6-((trans)-4-tert-butylcyclohexyloxy)naphthalen-2-yl)propan-2-amine (113 mg, 0.33 mmol, 1.0 eq.) and methyl acrylate (86 mg, 0.99 mmol, 3.0 eq.) was dissolved in MeOH (2 mL). The mixture was reflux for 16 h. The mixture was concentrated and purified by silica gel chromatography (DCM:MeOH=20:1) to give the title compound (100 mg, 71%) as a slight yellow oil. 1H NMR (400 MHz, CDCl3) δ: 7.73-7.68 (m, 3H), 7.60 (dd, 1H), 7.13-7.16 (m, 2H), 4.26-4.23 (m, 1H), 3.66 (s, 3H), 2.62 (t, 2H), 2.50 (t, 2H), 2.28-2.26 (m, 2H), 1.90-1.87 (m, 2H), 1.58 (s, 6H), 1.45-1.38 (m, 2H), 1.19-1.09 (m, 3H), 0.89 (s, 9H).

Workup

  1. temperatureThe mixture was reflux for 16 h
  2. concentrationThe mixture was concentrated
  3. custompurified by silica gel chromatography (DCM:MeOH=20:1)

Sources & evidence

ORD record
ord-b1495d1b9a6c4b9781835eaf7078fdca
Source dataset
uspto-grants-2014_08
Patent number
US08802659B2

Reaction notes

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