Tetrabutylammonium Fluoride → 3-Hydroxy-1-(4-morpholinocarbonyl-1,3-oxazol-2-yl)azetidine

HRID 891809Notes

Reaction equation

HRID 891809 reaction equation
[Si]([O:18][CH:19]1[CH2:22][N:21]([C:23]2[O: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>[OH:18][CH:19]1[CH2:20][N:21]([C:23]2[O: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)[CH2:22]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 222428193-t-Butyldiphenylsilyloxy-1-(4-morpholinocarbonyl-1,3-oxazol-2-yl)azetidine

Product 1

HCID 222429883-Hydroxy-1-(4-morpholinocarbonyl-1,3-oxazol-2-yl)azetidineYield 100.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-t-butyldiphenylsilyloxy-1-(4-morpholinocarbonyl-1,3-oxazol-2-yl)azetidine (730 mg, 1.48 mmol) (obtained as described in Reference Example 72(1)) in anhydrous tetrahydrofuran (37 ml) was added a solution of 1.0 M tetra-n-butylammonium fluoride in tetrahydrofuran (1.78 ml, 1.78 mmol) in an ice bath and the mixture was stirred in an ice bath for 1.5 hours. 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:methanol (95:5→9:1) as the eluant to afford 3-hydroxy-1-(4-morpholinocarbonyl-1,3-oxazol-2-yl)azetidine (377 mg, yield 100%) as white 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-dad8d1a42d67417e9b621675ea235ead
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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