Methyl Acrylate → HCID 178464347, compound

HRID 2404132Notes

Reaction equation

HRID 2404132 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]([CH2:22][NH:23][CH2:24][CH3:25])[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]([CH2:22][N:23]([CH2:24][CH3:25])[CH2:28][CH2:27][C:26]([O:30][CH3:31])=[O:29])[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 7294Methyl AcrylateHCID 178463667HCID 178463667, compound

Product 1

HCID 178464347HCID 178464347, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-((6-((trans)-4-tert-butylcyclohexyloxy)naphthalen-2-yl)methyl)ethanamine (250 mg, 0.64 mmol, 1 equiv) was dissolved in CH3OH (1 mL). Then methyl acrylate (4 mL, 44 mmol, 70 equiv) was added to the mixture and stirred at r.t. for 16 h. The reaction was concentrated and purified by prep-TLC to give the title compound as a white solid (217 mg, 52%). (mobile phase: EA/PE=1:8). ESI-MS (M+1)+: 426.3, HPLC: 97.34%. 1H NMR (400 MHz, CDCl3) δ: 7.71˜7.60 (m, 3H), 7.44˜7.38 (m, 1H), 7.16˜7.09 (m, 2H), 4.30˜4.20 (m, 1H), 3.69 (s, 2H), 3.64 (s, 3H), 2.85 (t, 2H), 2.65˜2.46 (m, 4H), 2.31˜2.24 (m, 2H), 1.92˜1.85 (m, 2H), 1.49˜1.37 (m, 2H), 1.30˜1.10 (m, 3H), 1.05 (t, 3H), 0.89 (s, 9H).

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by prep-TLC

Sources & evidence

ORD record
ord-e5a05a14aa2546188dfe74b6c8c67340
Source dataset
uspto-grants-2014_08
Patent number
US08802659B2

Reaction notes

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