Diisopropylethylamine → [2-(2,6-Dimethyl-4-prop-1-ynyl-phenyl)-3-oxo-4-(2-pyridylmethyl)cyclopenten-1-yl]isopropylsulfanylformate

HRID 514218Notes

Reaction equation

HRID 514218 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]#[C:9][CH3:10])[CH:5]=[C:4]([CH3:11])[C:3]=1[CH:12]1[C:16](=[O:17])[CH:15]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH2:14][C:13]1=[O:25].C(N(C(C)C)C(C)C)C.Cl[C:36]([S:38][CH:39]([CH3:41])[CH3:40])=[O:37]>ClCCl>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]#[C:9][CH3:10])[CH:5]=[C:4]([CH3:11])[C:3]=1[C:12]1[C:16](=[O:17])[CH:15]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH2:14][C:13]=1[O:25][C:36]([S:38][CH:39]([CH3:41])[CH3:40])=[O:37]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 13279441S-Isopropyl chlorothioformateHCID 896008972-(2,6-Dimethyl-4-prop-1-ynyl-phenyl)-4-(2-pyridylmethyl)cyclopentane-1,3-dione

Product 1

HCID 89601279[2-(2,6-Dimethyl-4-prop-1-ynyl-phenyl)-3-oxo-4-(2-pyridylmethyl)cyclopenten-1-yl]isopropylsulfanylformateYield 18%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the 2-(2,6-dimethyl-4-prop-1-ynyl-phenyl)-4-(2-pyridylmethyl)cyclopentane-1,3-dione (0.100 g, 0.302 mmol) in dichloromethane (3.02 mL) was added N-ethyl-N-isopropyl-propan-2-amine (1.51 mmol, 0.265 mL). The reaction was then cooled in the freezer for 30 minutes before addition of S-isopropyl chlorothioformate (0.075 ml, 0.603 mmol), and then the reaction mixture was stirred overnight at room temperature. The reaction was then washed with water, dried and reduced in vacuo. The crude product was then purified by column chromatography, eluting with acetonitrile and dichloromethane, to give the desired product (23 mg, 18%). The product was characterised by HPLC, as follows.

Workup

  1. washThe reaction was then washed with water
  2. customdried
  3. customThe crude product was then purified by column chromatography
  4. washeluting with acetonitrile and dichloromethane

Sources & evidence

ORD record
ord-869a7fe3fa5d4900ac448906fc249847
Source dataset
uspto-grants-2015_08
Patent number
US09107415B2

Reaction notes

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