Tetrabutylammonium Fluoride → HCID 18727232, compound

HRID 366498Notes

Reaction equation

HRID 366498 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([Si](C(C)C)(C(C)C)[N:23]1[CH:27]=[CH:26][C:25]([CH:28]2[CH2:33][CH2:32][N:31]([S:34]([N:37]3[CH2:42][CH2:41][CH2:40][CH2:39][C@@H:38]3[C:43]([O:45][CH3:46])=[O:44])(=[O:36])=[O:35])[CH2:30][CH2:29]2)=[CH:24]1)(C)C>O1CCCC1.C(OCC)(=O)C>[NH:23]1[CH:27]=[CH:26][C:25]([CH:28]2[CH2:29][CH2:30][N:31]([S:34]([N:37]3[CH2:42][CH2:41][CH2:40][CH2:39][C@@H:38]3[C:43]([O:45][CH3:46])=[O:44])(=[O:36])=[O:35])[CH2:32][CH2:33]2)=[CH:24]1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 53787954HCID 53787954, compound

Product 1

HCID 18727232HCID 18727232, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tetrabutylammonium fluoride (2.45 ml, 2.45 mmol) was added to a solution of methyl 1-[4-(1-triisopropylsilylpyrrol-3-yl)piperidine-1-sulfonyl]piperidine-2-(R)-carboxylate (2.5 g, 4.89 mmol) [prepared as described in Step 2 above] in tetrahydrofuran (48 ml) at 0° C. After 30 min., the reaction mixture was diluted with ethyl acetate, washed with water, brine, dried over MgSO4, and concentrated in vacuo. The residue was chromatographed (SiO2, 15-40% ethyl acetate/hexanes) to yield methyl 1-[4-(pyrrol-3-yl)piperidine-1-sulfonyl]piperidine-2-(R)-carboxylate (31%) as a clear oil. This material was converted to 1-[4-(pyrrol-3-yl)-piperidine-1-sulfonyl]piperidine-2-(R)-carboxylic acid (93%) by proceeding as described in Example 11, Step 1, but substituting methyl (R)-2-{[4-(5-chloropyridin-2-yloxy)piperidine-1 sulfonyl]amino}-3-methylbutyrate with methyl 1-[4-(pyrrol-3-yl)piperidine-1-sulfonyl]-piperidine-2-(R)-carboxylate.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was chromatographed (SiO2, 15-40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-ea142fa0e4174747b4831fd6bba4f707
Source dataset
uspto-grants-2000_10
Patent number
US06130220

Reaction notes

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