Methyl Acrylate → HCID 178500792, compound

HRID 713917Notes

Reaction equation

HRID 713917 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-52cd9cd26a364b7ea9314a18f92f865c
Source dataset
uspto-grants-2015_11
Patent number
US09186367B2

Reaction notes

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