Triethylamine → HCID 178455339, compound

HRID 2235234Notes

Reaction equation

HRID 2235234 reaction equation
[Cl:1][C:2]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:3]=1[CH2:4][CH:5]1[CH2:9][CH2:8][N:7]([C@H:10]2[CH2:15][CH2:14][C@@H:13]([OH:16])[CH2:12][CH2:11]2)[C:6]1=[O:17].C(N(CC)CC)C.FC(F)(F)S(O[Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])(=O)=O>ClCCl>[Cl:1][C:2]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:3]=1[CH2:4][CH:5]1[CH2:9][CH2:8][N:7]([C@H:10]2[CH2:11][CH2:12][C@@H:13]([O:16][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])[CH2:14][CH2:15]2)[C:6]1=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 178515595HCID 178515595, compound

Product 1

HCID 178455339HCID 178455339, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 3-(2,4-dichloro-benzyl)-1-(cis-4-hydroxy-cyclohexyl)-pyrrolidin-2-one (0.5 g, 1.46 mmol) in dichloromethane (15 mL), cool to 0° C., and add triethylamine (0.26 mL, 1.90 mmol) and t-butyldimethylsilyl trifluoromethanesulfonate (0.40 mL, 1.75 mmol). After 16 h, wash the mixture with 1 N HCl, saturated aqueous NaHCO3 and brine, dry over Na2SO4 and evaporate the solvent. Purify the residue by column chromatography on silica gel (eluting 0% to 40% ethyl acetate in hexanes) to give the desired intermediate (0.54 g, 81%).

Workup

  1. washwash the mixture with 1 N HCl, saturated aqueous NaHCO3 and brine
  2. dry with materialdry over Na2SO4
  3. customevaporate the solvent
  4. customPurify the residue by column chromatography on silica gel (eluting 0% to 40% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-64deb78c3ceb425cbef3781b10956800
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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