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

HRID 891561Notes

Reaction equation

HRID 891561 reaction equation
[Si]([O:18][CH:19]1[CH2:22][N:21]([C:23]2[S:24][CH:25]=[C:26]([C:28]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)=[O: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>[O:33]1[CH2:32][CH2:31][N:30]([C:28]([C:26]2[N:27]=[C:23]([N:21]3[CH2:22][CH:19]([OH:18])[CH2:20]3)[S:24][CH:25]=2)=[O:29])[CH2:35][CH2:34]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 222427403-t-Butyldiphenylsilyloxy-1-(4-morpholinocarbonyl-1,3-thiazol-2-yl)azetidine

Product 1

HCID 222428331-(4-Morpholinocarbonyl-1,3-thiazol-2-yl)-3-hydroxyazetidineYield 97.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-t-butyldiphenylsilyloxy-1-(4-morpholinocarbonyl-1,3-thiazol-2-yl)azetidine (1.05 g, 2.07 mmol) (obtained as described in Reference Example 11(1)) in anhydrous tetrahydrofuran (32 ml) was added a solution of 1.0M tetra-n-butylammonium fluoride in tetrahydrofuran (2.48 ml, 2.48 mmol) and the reaction mixture was stirred for 1 hour. After checking the completion of the reaction, the reaction mixture was concentrated under reduced pressure and the residue was purified by chromatography on a silica gel column using ethyl acetate→10% methanol in ethyl acetate as the eluant to afford 1-(4-morpholinocarbonyl-1,3-thiazol-2-yl)-3-hydroxyazetidine (542 mg, yield 97%) 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-d41d3cbf70014feabda9351de30332ad
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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