(2S,4R)-1-allyloxycarbonyl-4-t-butyldimethylsilyloxy-2-formylpyrrolidine → HCID 20639575, compound

HRID 568291Notes

Reaction equation

HRID 568291 reaction equation
[CH3:1][S:2][C:3]1[N:10]2[C:6]([S:7][CH:8]=[CH:9]2)=[CH:5][N:4]=1.[CH2:11]([O:14][C:15]([N:17]1[C@H:21]([CH:22]=[O:23])[CH2:20][C@@H:19]([O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])[CH2:18]1)=[O:16])[CH:12]=[CH2:13]>>[CH2:11]([O:14][C:15]([N:17]1[C@H:21]([CH:22]([OH:23])[C:8]2[S:7][C:6]3=[CH:5][N:4]=[C:3]([S:2][CH3:1])[N:10]3[CH:9]=2)[CH2:20][C@@H:19]([O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:26])[CH3:27])[CH2:18]1)=[O:16])[CH:12]=[CH2:13]

Participants

3

Reactant 2

HCID 22870383(2S,4R)-1-allyloxycarbonyl-4-t-butyldimethylsilyloxy-2-formylpyrrolidineHCID 234491605-Methylthioimidazo[5,1-b]thiazole

Product 1

HCID 20639575HCID 20639575, compoundYield 52.1%

Procedure

The procedure of Synthesis Example 10-a) is repeated, except that 1.60 g of 5-methylthioimidazo[5,1-b]thiazole and 2.97 g of (3R,5S)-1-allyloxycarbonyl-3-t-butyldimethylsilyloxy-5-formylpyrrolidine are used and the purification is successively performed by column chromatography on Sephadex LH-20 (dichloromethane:methanol=1:1) and on silica gel (hexane:ethyl acetate=1:2) to give 2.37 g of (3R,5S)-1-allyloxycarbonyl-3-t-butyldimethylsilyloxy-5-[1-hydroxy-1-(5-methylthioimidazo[5,1-b]thiazol-2-yl)methyl]pyrrolidine (a diastereomer mixture) as a yellow amorphous material.

Workup

  1. customThe procedure of Synthesis Example 10-a)
  2. customthe purification

Sources & evidence

ORD record
ord-cfcb4f1f558a4d1aaa86298e3e3934e1
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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