Di-tert-butyl dicarbonate → 2-(4-Hydroxy-phenyl)-morpholine-4-carboxylic acid

HRID 588245Notes

Reaction equation

HRID 588245 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH:3]([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH2:2]1.[C:14](OC(OC(C)(C)C)=O)([O:16]C(C)(C)C)=[O:15]>CC#N>[OH:13][C:10]1[CH:11]=[CH:12][C:7]([CH:3]2[O:4][CH2:5][CH2:6][N:1]([C:14]([OH:16])=[O:15])[CH2:2]2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 538045794-(Morpholin-2-yl)phenol

Product 1

HCID 775535902-(4-Hydroxy-phenyl)-morpholine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-morpholin-2-yl-phenol (0.99 g; 5.41 mmol) and di-tert-butyl dicarbonate (1.18 g; 5.41 mmol) in CH3CN (50 mL) was stirred at RT for 3 days. Subsequently, the resulting mixture was concentrated in vacuo and the residue was purified by column chromatography (SiO2, CH2Cl2:CH3OH 97:3) to afford 2-(4-hydroxy-phenyl)-morpholine-4-carboxylic acid tort-butyl ester (1.15 g).

Workup

  1. concentrationSubsequently, the resulting mixture was concentrated in vacuo
  2. customthe residue was purified by column chromatography (SiO2, CH2Cl2:CH3OH 97:3)

Sources & evidence

ORD record
ord-15298b50d539498f9c56e6a414f736d4
Source dataset
uspto-grants-2016_01
Patent number
US09227960B2

Reaction notes

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