Aniline → 1-t-Butoxycarbonyl-3-hydroxy-4-phenylaminopyrrolidine

HRID 2293991

Reaction equation

HRID 2293991 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]2[O:13][CH:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:11]([OH:13])[CH2:12]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 6115AnilineHCID 10103880tert-Butyl 6-Oxa-3-azabicyclo(3.1.0)hexane-3-carboxylate

Product 1

HCID 214733471-t-Butoxycarbonyl-3-hydroxy-4-phenylaminopyrrolidineYield 64.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 20 ml of ethyl alcohol was dissolved 5 g (0.027 mole) of 1-t-butoxycarbonyl-3-epoxypyrrolidine, and 12.6 g (0.135 mole) of aniline was added thereto. The mixture was refluxed by heating for 20 hours. After the mixture was cooled to room temperature, the solvent was removed under reduced pressure, and the residue was applied to silica gel column chromatography (the eluent used was a mixture of ethyl acetate:toluene=1:4) to obtain 4.85 g of 1-t-butoxycarbonyl-3-hydroxy-4-phenylaminopyrrolidine as yellowish brown crystals.

Workup

  1. additionwas added
  2. temperatureThe mixture was refluxed
  3. temperatureby heating for 20 hours
  4. customthe solvent was removed under reduced pressure
  5. additiona mixture of ethyl acetate

Sources & evidence

ORD record
ord-cc48a11a0c6f4f92a7fee401fa3e0cd9
Source dataset
uspto-grants-1997_11
Patent number
US05688791

Linked notes

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