Methyl 2-(hydroxymethyl)prop-2-enoate → HCID 178500921, compound

HRID 713913Notes

Reaction equation

HRID 713913 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][NH2:23])[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[OH:24][CH2:25][C:26](=[CH2:31])[C:27]([O:29][CH3:30])=[O: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][NH:23][CH2:31][CH:26]([CH2:25][OH:24])[C:27]([O:29][CH3:30])=[O:28])[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 11815329Methyl 2-(hydroxymethyl)prop-2-enoateHCID 178445772HCID 178445772, compound

Product 1

HCID 178500921HCID 178500921, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compounds (6-((trans)-4-tert-butylcyclohexyloxy)naphthalen-2-yl)methanamine (311 mg, 1.0 mmol, 1.0 eq.) and methyl 2-(hydroxymethyl)acrylate (116 mg, 1.0 mmol, 1.0 eq.) was dissolved in MeOH (5 mL). The mixture was stirred at r.t. for 2 h. Then the mixture was concentrated and purified by silica gel column chromatography using DCM/CH3OH (10/1) to give product (250 mg, 58%) as a slight yellow oil. ESI-MS (M+H)+: 428.3. HPLC: 90.18%. 1H NMR (400 MHz, CDCl3) δ 7.68 (t, 2H), 7.63 (s, 1H), 7.37 (dd, 1H), 7.14-7.11 (m, 2H), 4.27-4.25 (m, 1H), 4.01-3.96 (m, 2H), 3.91 (s, 2H), 3.71 (s, 3H), 3.18-2.93 (AB, 2H), 2.73-2.71 (m, 1H), 2.28-2.25 (m, 2H), 1.90-1.87 (m, 2H), 1.45-1.40 (m, 2H), 1.25-1.09 (m, 3H), 0.89 (s, 9H).

Workup

  1. concentrationThen the mixture was concentrated
  2. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-9260aa2e08af4e50a763fdfacd7f0dbc
Source dataset
uspto-grants-2015_11
Patent number
US09186367B2

Reaction notes

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