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

HRID 891564Notes

Reaction equation

HRID 891564 reaction equation
[Si]([O:18][CH:19]1[CH2:22][N:21]([C:23]2[S:24][CH:25]=[C:26]([CH2:28][OH: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:29][CH2:28][C:26]1[N:27]=[C:23]([N:21]2[CH2:22][CH:19]([OH:18])[CH2:20]2)[S:24][CH:25]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 222428843-t-Butyldiphenylsilyloxy-1-(4-hydroxymethyl-1,3-thiazol-2-yl)azetidine

Product 1

HCID 222430061-(4-Hydroxymethyl-1,3-thiazol-2-yl)-3-hydroxyazetidineYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-t-butyldiphenylsilyloxy-1-(4-hydroxymethyl-1,3-thiazol-2-yl)azetidine (548.5 mg, 1.29 mmol) (obtained as described in Reference Example 2(2)) in anhydrous tetrahydrofuran (28 ml) was added a solution of 1.0M tetra-n-butylammonium fluoride in tetrahydrofuran (1.56 ml, 1.56 mmol) in an ice bath, and the mixture was then 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 ethyl acetate:methanol (10:1) as the eluant to afford 1-(4-hydroxymethyl-1,3-thiazol-2-yl)-3-hydroxyazetidine (230 mg, yield 96%) 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-c06b0b6b586c48d988b8e0b3ababfc13
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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