Tetrabutylammonium Fluoride → HCID 69544102, compound

HRID 891579Notes

Reaction equation

HRID 891579 reaction equation
[Si]([O:18][C@@H:19]1[CH2:23][CH2:22][N:21]([C:24]2[S:25][CH:26]=[C:27]([C:29](=[O:31])[NH2:30])[N:28]=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:29]([C:27]1[N:28]=[C:24]([N:21]2[CH2:22][CH2:23][C@@H:19]([OH:18])[CH2:20]2)[S:25][CH:26]=1)(=[O:31])[NH2:30]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69544087HCID 69544087, compound

Product 1

HCID 69544102HCID 69544102, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (3R)-3-t-butyldiphenylsilyloxy-1-(4-carbamoyl-1,3-thiazol-2-yl)pyrrolidine (950 mg, 2.10 mmol) (obtained as described in Reference Example 18(5)) in anhydrous tetrahydrofuran (20 ml) was added a solution of 1.0M tetra-n-butylammonium fluoride in tetrahydrofuran (2.52 ml, 2.52 mmol) in an ice bath. The mixture was stirred at room temperature 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 n-hexane:ethyl acetate (1:1)→10% methanol in ethyl acetate as the eluant to afford (3R)-1-(4-carbamoyl-1,3-thiazol-2-yl)-3-hydroxypyrrolidine (428 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-0536e487b9f2460980b4f428ba5d3e99
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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