Tributylstannane → (3R,5s)-1-allyloxycarbonyl-3-t-butyldimethylsilyloxy-5-(5-chloroimidazo[5,1-b]thiazol-2-yl)methylpyrrolidine

HRID 568295Notes

Reaction equation

HRID 568295 reaction equation
C([SnH](CCCC)CCCC)CCC.N(C(C)(C)C#N)=NC(C)(C)C#N.[CH2:26]([O:29][C:30]([N:32]1[C@H:36]([CH:37]([C:43]2[S:47][C:46]3=[CH:48][N:49]=[C:50]([Cl:51])[N:45]3[CH:44]=2)OC(SC)=S)[CH2:35][C@@H:34]([O:52][Si:53]([C:56]([CH3:59])([CH3:58])[CH3:57])([CH3:55])[CH3:54])[CH2:33]1)=[O:31])[CH:27]=[CH2:28]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:26]([O:29][C:30]([N:32]1[C@H:36]([CH2:37][C:43]2[S:47][C:46]3=[CH:48][N:49]=[C:50]([Cl:51])[N:45]3[CH:44]=2)[CH2:35][C@@H:34]([O:52][Si:53]([C:56]([CH3:59])([CH3:58])[CH3:57])([CH3:54])[CH3:55])[CH2:33]1)=[O:31])[CH:27]=[CH2:28]

Participants

6

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 20639569(3R,5S)-1-allyloxycarbonyl-3-t-butyldimethylsilyloxy-5-[1-(5-chloroimidazo[5,1-b]thiazol-2-yl)-1-(methylthiothiocarbonyloxy)methyl]pyrrolidine

Product 1

HCID 20639583(3R,5s)-1-allyloxycarbonyl-3-t-butyldimethylsilyloxy-5-(5-chloroimidazo[5,1-b]thiazol-2-yl)methylpyrrolidineYield 71.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Tri-n-butyltin hydride (1.8 ml) and 147 mg of 2,2′-azobisisobutyronitrile are added to a solution of 2.520 g of (3R,5S)-1-allyloxycarbonyl-3-t-butyldimethylsilyloxy-5-[1-(5-chloroimidazo[5,1-b]thiazol-2-yl)-1-(methylthiothiocarbonyloxy)methyl]pyrrolidine (a diastereomer mixture) in 22.5 ml of dry toluene, and the mixture is stirred in an argon atmosphere at an external temperature of 80° C. for 90 min. The reaction solution is diluted with 200 ml of ethyl acetate, washed with semi-saturated saline and dried over anhydrous magnesium sulfate. The solvent is removed by evaporation under reduced pressure to give a crude product which is then purified by column chromatography on silica gel (hexane:ethyl acetate=2:1) to give 1.467 g of (3R,5s)-1-allyloxycarbonyl-3-t-butyldimethylsilyloxy-5-(5-chloroimidazo[5,1-b]thiazol-2-yl)methylpyrrolidine as a slightly yellow oil.

Workup

  1. washwashed with semi-saturated saline
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent is removed by evaporation under reduced pressure
  4. customto give a crude product which
  5. customis then purified by column chromatography on silica gel (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-93eddc677cfb45e1b1213dfb8b6c8303
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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