Ethyl glycidate → HCID 178473108, compound

HRID 713909Notes

Reaction equation

HRID 713909 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].[O:24]1[CH2:26][CH:25]1[C:27]([O:29][CH2:30][CH3:31])=[O:28]>CCO>[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][CH2:26][CH:25]([OH:24])[C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 107319Ethyl glycidateHCID 178445772HCID 178445772, compound

Product 1

HCID 178473108HCID 178473108, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(6-((trans)-4-tert-butylcyclohexyloxy)naphthalen-2-yl)methanamine (311 mg, 1.0 mmol, 1.0 eq.) and ethyl oxirane-2-carboxylate (116 mg, 1.0 mmol, 1.0 eq.) was dissolved in EtOH (5 mL). Then the mixture was refluxed for 2 h. The mixture was concentrated and purified by silica gel column chromatography using DCM/MeOH (10/1) as eluent to give product as a slight yellow oil (311 mg, 35%). EDI-MS (M+1)+: 428.1. HPLC: 92.02%. 1H NMR (400 MHz, CDCl3) δ 7.70-7.64 (m, 3H), 7.38 (dd, 1H), 7.13-7.11 (m, 2H), 4.31-4.21 (m, 4H), 3.93 (q, 2H), 3.06-2.88 (AB, 2H), 2.60 (b, 2H), 2.28-2.26 (m, 2H), 1.90-1.87 (m, 2H), 1.45-1.41 (m, 2H), 1.26 (t, 3H), 1.20-1.09 (m, 3H), 0.89 (s, 9H).

Workup

  1. temperatureThen the mixture was refluxed for 2 h
  2. concentrationThe mixture was concentrated
  3. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-0732e0f155a94ac98d4a5d7c1867a7e4
Source dataset
uspto-grants-2015_11
Patent number
US09186367B2

Reaction notes

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