Tetrabutylammonium Fluoride → HCID 69543998, compound

HRID 891587Notes

Reaction equation

HRID 891587 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 69544156HCID 69544156, compound

Product 1

HCID 69543998HCID 69543998, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (3S)-3-t-butyldiphenylsilyloxy-1-(4-carbamoyl-1,3-thiazol-2-yl)pyrrolidine (3.1 g, 6.86 mmol) (obtained as described in Reference Example 20(6)) in anhydrous tetrahydrofuran (90 ml) was added a solution of 1.0M tetra-n-butylammonium fluoride in tetrahydrofuran (8.24 ml, 8.24 mmol) in an ice bath, and the mixture was stirred 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→10% methanol in ethyl acetate as the eluant to afford (3S)-1-(4-carbamoyl-1,3-thiazol-2-yl)-3-hydroxypyrrolidine (1.42 g, yield 98%) 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-242238176b3e47eaa51ead5601a90f53
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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