Tetrabutylammonium Fluoride → 1-(4-Cyano-1,3-thiazol-2-yl)-3-hydroxyazetidine

HRID 891557Notes

Reaction equation

HRID 891557 reaction equation
[Si]([O:18][CH:19]1[CH2:22][N:21]([C:23]2[S:24][CH:25]=[C:26]([C:28]#[N:29])[N:27]=2)[CH2:20]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:28]([C:26]1[N:27]=[C:23]([N:21]2[CH2:22][CH:19]([OH:18])[CH2:20]2)[S:24][CH:25]=1)#[N:29]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 222430073-t-Butyldiphenylsilyloxy-1-(4-cyano-1,3-thiazol-2-yl)azetidine

Product 1

HCID 222427171-(4-Cyano-1,3-thiazol-2-yl)-3-hydroxyazetidineYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-t-butyldiphenylsilyloxy-1-(4-cyano-1,3-thiazol-2-yl)azetidine (2.36 g, 5.62 mmol) (obtained as described in Reference Example 4(1)) in anhydrous tetrahydrofuran (115 ml) was added a solution of 1.0M tetra-n-butylammonium fluoride in tetrahydrofuran (6.7 ml, 6.7 mmol) in an ice bath. The mixture was stirred in the ice bath for 1 hour. 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 toluene:ethyl acetate (1:2) as the eluant to afford 1-(4-cyano-1,3-thiazol-2-yl)-3-hydroxyazetidine (0.78 g, yield 77%) as a white solid.

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-2dcd75651f564a919e0a0a0b04d3f6c8
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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