2-(1-Hydroxy-2-phenethyl-4-phenyl-butyl)-pyrrolidine-1-carboxylic acid tert-butyl ester → 2-(2-Phenethyl-4-phenyl-butyryl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1828067Notes

Reaction equation

HRID 1828067 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[C:12]([O:16][C:17]([N:19]1[CH2:23][CH2:22][CH2:21][CH:20]1[CH:24]([OH:42])[CH:25]([CH2:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:18])([CH3:15])([CH3:14])[CH3:13]>C(Cl)Cl>[C:12]([O:16][C:17]([N:19]1[CH2:23][CH2:22][CH2:21][CH:20]1[C:24](=[O:42])[CH:25]([CH2:34][CH2:35][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

4

Reactant 2

HCID 210277702-(1-Hydroxy-2-phenethyl-4-phenyl-butyl)-pyrrolidine-1-carboxylic acid tert-butyl esterHCID 178418287HCID 178418287, compound

Product 1

HCID 210277712-(2-Phenethyl-4-phenyl-butyryl)-pyrrolidine-1-carboxylic acid tert-butyl esterYield 76.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.22 g (1.0 mmol) of pyridinium chlorochromate in anhydrous CH2Cl2 (15 mL) was added dropwise a solution of 0.2 g (0.5 mmol) of 10a in anhydrous CH2Cl2 (5 mL), and the mixture was stirred at an ambient temperature for 16 hours. The solution was filtered and the resulting solution was evaporated to a yellow oil which was subject to column chromatography (EtOAc/Hexanes, 1:3) to yield 0.16 g (76.2%) of 11a as a clear oil. TLC Rf=0.5 (EtOAc/Hexanes, 1:3)

Workup

  1. filtrationThe solution was filtered
  2. customthe resulting solution was evaporated to a yellow oil which

Sources & evidence

ORD record
ord-8e2e8e8458484e86805a7e28468a39e3
Source dataset
uspto-grants-2006_06
Patent number
US07056935B2

Reaction notes

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