Pyrrolidine → HCID 58869197, compound

HRID 2355199Notes

Reaction equation

HRID 2355199 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:15](=[O:17])[CH3:16].[C:18]([O:22][C:23](=[O:29])[N:24]([CH3:28])[CH2:25][CH:26]=O)([CH3:21])([CH3:20])[CH3:19].N1CCCC1>C1(C)C=CC=CC=1>[C:18]([O:22][C:23](=[O:29])[N:24]([CH3:28])[CH2:25][CH:26]1[CH2:16][C:15](=[O:17])[C:3]2[C:2](=[CH:7][C:6]([S:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[CH:5][CH:4]=2)[O:1]1)([CH3:20])([CH3:21])[CH3:19]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 10725881tert-butyl N-methyl-N-(2-oxoethyl)carbamateHCID 58869175HCID 58869175, compound

Product 1

HCID 58869197HCID 58869197, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1-(2-hydroxy-4-phenylsulfanyl-phenyl)-ethanone (244 mg, 1 mmol) and methyl-(2-oxo-ethyl)-carbamic acid tert-butyl ester (259 mg, 1.5 mmol) (Tetrahedron 58, 2002, 1719-37) in toluene (25 mL) was added pyrrolidine (71 mg, 1 mmol). The reaction was stirred at room temperature for 60 hours. The mixture was concentrated in vacuo and the residue was purified via flash chromatography (hexane/Et2O, 3/1) to give methyl-(4-oxo-7-phenylsulfanyl-chroman-2-ylmethyl)-carbamic acid tert-butyl ester (134 mg, 34% yield) as clear oil.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was purified via flash chromatography (hexane/Et2O, 3/1)

Sources & evidence

ORD record
ord-eeb9eaa9b9f345fd84d0ec68ed6f16ad
Source dataset
uspto-grants-2010_07
Patent number
US07754759B2

Reaction notes

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