tert-Butyldimethylsilyl chloride → HCID 66877225, compound

HRID 503946Notes

Reaction equation

HRID 503946 reaction equation
[C:1]([Si:5]([CH3:8])([CH3:7])Cl)([CH3:4])([CH3:3])[CH3:2].[C:9]([O:13][C:14]([N:16]1[CH2:20][CH2:19][C@@H:18]([C:21]2[CH:26]=[CH:25][C:24]([S:27]([C:30]3[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=3)(=[O:29])=[O:28])=[CH:23][CH:22]=2)[CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].OS([O-])(=O)=O.[K+].[O-]S([O-])(=O)=O.[Na+].[Na+]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:9]([O:13][C:14]([N:16]1[CH2:20][CH2:19][C@@H:18]([C:21]2[CH:26]=[CH:25][C:24]([S:27]([C:30]3[CH:35]=[CH:34][C:33]([O:36][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:8])[CH3:7])=[CH:32][CH:31]=3)(=[O:29])=[O:28])=[CH:23][CH:22]=2)[CH2:17]1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

6

Reactant 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 66877544HCID 66877544, compoundHCID 86586342KHSO4 Na2SO4

Product 1

HCID 66877225HCID 66877225, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

t-Butyldimethylchlorosilane (116.55 mg, 0.773 mmol), TEA (0.1336 mL, 0.975 mmol) and DMAP (9 mg, 0.0736 mmol) were added to a solution of (S)-3-[4-(4-hydroxy-benzenesulfonyl)-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (297 mg, 0.736 mmol) in DCM (5 mL) under argon atmosphere. The reaction mixture was stirred at room temperature for 3 hours. and then a solution of 10% KHSO4/Na2SO4 was added. The mixture was extracted with DCM, and the combined organic extracts were washed with NaHCO3 (10% aqueous solution), dried over Na2SO4, filtered, and evaporated under reduced pressure. The resulting crude material was purified via flash chromatography (hexane/EtOAc, 783/17) to give 370.6 mg (97% yield) of (S)-3-{4-[4-(tert-butyl-dimethyl-silanyloxy)-benzenesulfonyl]-phenyl}-pyrrolidine-1-carboxylic acid tert-butyl ester as a foam.

Workup

  1. extractionThe mixture was extracted with DCM
  2. washthe combined organic extracts were washed with NaHCO3 (10% aqueous solution)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe resulting crude material was purified via flash chromatography (hexane/EtOAc, 783/17)

Sources & evidence

ORD record
ord-fdcfb075c5914e68b35e79537ca1563c
Source dataset
uspto-grants-2010_08
Patent number
US07776910B2

Reaction notes

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