Tetrabutylammonium Fluoride → HCID 22242912, compound

HRID 891681Notes

Reaction equation

HRID 891681 reaction equation
[CH2:1]([O:4][C:5]([C:7]1[N:8]=[C:9]([N:12]2[CH2:15][CH:14]([O:16][Si](C(C)(C)C)(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:13]2)[S:10][CH:11]=1)=[O:6])[CH:2]=[CH2:3].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:1]([O:4][C:5]([C:7]1[N:8]=[C:9]([N:12]2[CH2:13][CH:14]([OH:16])[CH2:15]2)[S:10][CH:11]=1)=[O:6])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 222427721-(4-Allyloxycarbonyl-1,3-thiazol-2-yl)-3-t-butyldiphenylsilyloxyazetidine

Product 1

HCID 22242912HCID 22242912, compoundYield 109.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-(4-allyloxycarbonyl-1,3-thiazol-2-yl)-3-t-butyldiphenylsilyloxyazetidine (5.31 g, 11.1 mmol) (obtained as described in Reference Example 41(1)) in anhydrous tetrahydrofuran (266 ml) was added a solution of 1M tetrabutylammonium fluoride in tetrahydrofuran (13.3 ml, 13.3 mmol) in an ice bath. The mixture was stirred at room temperature overnight. After checking the completion of the reaction, the reaction mixture was concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using ethyl acetate as the eluant to afford 1-(4-allyloxycarbonyl-1,3-thiazol-2-yl)-3-hydroxyazetidine (2.91 g, yield 100%) as pale brown crystals.

Workup

  1. customthe completion of the reaction
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-9ee825e39fcc4d7c9ba9131204c3dec5
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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