HCID 178421967, compound → HCID 178421966, compound

HRID 2235312Notes

Reaction equation

HRID 2235312 reaction equation
[Cl:1][C:2]1[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:3]=1[CH2:4][C:5]1([CH3:25])[CH2:9][CH2:8][N:7]([C@H:10]2[CH2:15][CH2:14][C@@H:13]([O:16][Si](C(C)(C)C)(C)C)[CH2:12][CH2:11]2)[C:6]1=[O:24].ClC1C(C)=C(Cl)C=CC=1CC1(C)CCN([C@H]2CC[C@@H](O[Si](C(C)(C)C)(C)C)CC2)C1=O>C(O)C>[Cl:1][C:2]1[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:3]=1[CH2:4][C:5]1([CH3:25])[CH2:9][CH2:8][N:7]([C@H:10]2[CH2:11][CH2:12][C@@H:13]([OH:16])[CH2:14][CH2:15]2)[C:6]1=[O:24]

Participants

4

Reactant 2

HCID 178421967HCID 178421967, compoundHCID 178427919HCID 178427919, compound

Product 1

HCID 178421966HCID 178421966, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

Dissolve 3-(2,4-dichloro-benzyl)-1-(cis-4-t-butyldimethylsilyloxy-cyclohexyl)-3-methyl-pyrrolidin-2-one and 3-(2,4-dichloro-3-methyl-benzyl)-1-(cis-4-t-butyldimethylsilyloxy-cyclohexyl)-3-methyl-pyrrolidin-2-one (0.42 g, 0.89 mmol) in ethanol-2N HCl (1:1, 9 mL) and stir at 70° C. 2 h. Cool the mixture and partition between dichloromethane and saturated aqueous sodium bicarbonate and brine, dry the organic layer over sodium sulfate and evaporate. Purify the residue by column chromatography on silica gel (eluting 0% to 100% ethyl acetate in hexane) to give the desired product (97 mg, 31%). MS(ES+) m/z=356.

Workup

  1. custom2 h
  2. temperatureCool the mixture
  3. custompartition between dichloromethane and saturated aqueous sodium bicarbonate and brine
  4. dry with materialdry the organic layer over sodium sulfate
  5. customevaporate
  6. customPurify the residue by column chromatography on silica gel (eluting 0% to 100% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-747cf1e1abaf419baeee23cc6745890f
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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