Water → HCID 137331230, compound

HRID 1837981Notes

Reaction equation

HRID 1837981 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:30])=[CH:5][C:6]=1[C:7]1[CH:8]=[C:9]([C:13]#[C:14][C@H:15]([CH:17]2[N:21]([CH3:22])[C:20](=[O:23])[CH2:19][CH:18]2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[OH:16])[CH:10]=[CH:11][CH:12]=1.N1[C:36]([CH3:37])=[CH:35]C=CC=1C.[Si:39](OS(C(F)(F)F)(=O)=O)(C(C)(C)C)([CH3:41])[CH3:40].O.[CH2:55](Cl)Cl>>[CH3:1][C:2]1[NH:3][C:4]([CH3:30])=[CH:5][C:6]=1[C:7]1[CH:8]=[C:9]([C:13]#[C:14][C@@:15]([O:16][SiH:39]([CH3:41])[CH3:40])([C@@H:17]2[N:21]([CH3:22])[C:20](=[O:23])[CH2:19][C@@H:18]2[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:36]([CH3:35])([CH3:37])[CH3:55])[CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6344DichloromethaneHCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 69893256HCID 69893256, compound

Product 1

HCID 137331230HCID 137331230, compoundYield 47%

Procedure

To a 0° C. solution of (±)-(4R*5R*)-5-{(1R*)-3-[3-(2,5-dimethylpyrrolyl)phenyl]-1-hydroxyprop-2-ynyl}-1-methyl-4-phenylpyrrolidin-2-one (prepared according to the procedure described for Example 8, 0.15 g, 0.37 mmol) and 2,6-lutidine (0.1 mL, 0.93 mmol) in CH2Cl2 (10 mL) was added TBDMSOTf (0.13 mL, 0.55 mmol). The reaction mixture was stirred for 2 h, allowed to warm to room temperature and treated with water. The resulting mixture was extracted with CH2Cl2, dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by flash chromatography (80% EtOAc/hex) to give (±)-(4R*,5R*)-5-{(1R*)3-[3-(2,5-dimethylpyrrolyl)phenyl]-1-tert-butyldimethyl-silyloxyprop-2-ynyl}-1-methyl-4-phenylpyrrolidin-2-one (90 mg, 47%): mp 156-158° C.; TLC (50% EtOAc/hex) Rf 0.41.

Workup

  1. extractionThe resulting mixture was extracted with CH2Cl2
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by flash chromatography (80% EtOAc/hex)

Sources & evidence

ORD record
ord-82070bf04561434996740b09ea4e4776
Source dataset
uspto-grants-2004_08
Patent number
US06784167B2

Reaction notes

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