Phenyl glycidyl ether → HCID 54190254, compound

HRID 728903Notes

Reaction equation

HRID 728903 reaction equation
[C:1]([O:5][NH:6][C:7]([CH2:9][CH2:10][NH2:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].[O:12]([CH2:19][CH:20]1[O:22][CH2:21]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CO>[NH4+:6].[OH-:5].[C:1]([O:5][NH:6][C:7]([CH2:9][CH2:10][NH:11][CH2:21][CH:20]([OH:22])[CH2:19][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 31217Phenyl glycidyl etherHCID 15016310HCID 15016310, compound

Product 2

HCID 14923Ammonium HydroxideHCID 54190254HCID 54190254, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.0 g (6.2 mmol) of 2-(tert-butoxycarbamoyl)ethylamine and 940 mg (6.2 mmol) of (±)-3-phenoxy-1,2-epoxypropane in 15 ml of methanol is heated at reflux under N2 for 5 hr. After removing the solvent, the residue is flash chromatographed on silica gel (500 ml 98:2 CHCl3 :CH3OH, 500 ml of 95:5 CHCl3 :CH3OH, 500 ml of90:10 CHCl3 :CH3OH, and finally 1000 ml of 90:10:2 CHCl3 :CH3OH:NH4OH) to give 956 mg of (±)-N-(2-tertbutoxycarbamoylethyl)-2-hydroxy-3-phenoxypropylamine as a white solid. 1H-NMR (CDCl3): δ 1:55 (s,9H); 2.58-3.03 (m,6H); 3.30 (m,2H); 4.00 (d,2H); 4.17 (m,1H); 5.00 (s broad, 1H); 6.97 (m,3H); 7.30 (m,2H). Yield, 50 %.

Workup

  1. temperatureat reflux under N2 for 5 hr
  2. customAfter removing the solvent
  3. customchromatographed on silica gel (500 ml 98:2 CHCl3

Sources & evidence

ORD record
ord-397dc357ebc24763b0ce62ea313d59f8
Source dataset
uspto-grants-1991_09
Patent number
US05051431

Reaction notes

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