Triethylamine → HCID 18425759, compound

HRID 1280728Notes

Reaction equation

HRID 1280728 reaction equation
Br.[NH:2]1[CH2:6][CH2:5][CH:4]([S:7][C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH2:3]1.CCN([CH2:20][CH3:21])CC>C(Cl)Cl>[OH:14][C:11]1[CH:12]=[CH:13][C:8]([S:7][CH:4]2[CH2:5][CH2:6][N:2]([CH2:9][CH2:10][C:11](=[O:14])[CH2:12][C:21]3[CH:20]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:3]2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 18425768HCID 18425768, compound

Product 1

HCID 18425759HCID 18425759, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(RS)-4-(Pyrrolidin-3-ylsulfanyl)-phenol hydrobromide (470 mg, 1.7 mmol), Et3N (0.35 ml, 2.5 mmol) and 1-phenyl-3-butan-2-one (0.25 g, 1.7 mmol) were suspended in CH2Cl2 (10 ml). After stirring overnight at room temperature, the reaction mixture was concentrated and chromatographed over silica gel (hexane-ethylacetate 1:1 then ethylacetate) to provide (RS)-4-[3-(4-hydroxy-phenylsulfanyl)-pyrrolidin-1-yl]-1-phenyl-butan-2-one (90 mg, 16%) as a brown oil, MS: m/e 342.2 (M+H+).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customchromatographed over silica gel (hexane-ethylacetate 1:1

Sources & evidence

ORD record
ord-187fcc9e67fa4305a8e8986791bf8f0d
Source dataset
uspto-grants-2002_09
Patent number
US06451819B2

Reaction notes

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