Tetrabutylammonium Fluoride → 4-(5-Oxazol-5-yl-furo[2,3-c]pyridin-2-yl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1471782Notes

Reaction equation

HRID 1471782 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([C:32]2[O:55][C:35]3=[CH:36][N:37]=[C:38]([C:40]4[O:44][C:43]([Si](C(C)C)(C(C)C)C(C)C)=[N:42][CH:41]=4)[CH:39]=[C:34]3[CH:33]=2)[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]>O1CCCC1>[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([C:32]2[O:55][C:35]3=[CH:36][N:37]=[C:38]([C:40]4[O:44][CH:43]=[N:42][CH:41]=4)[CH:39]=[C:34]3[CH:33]=2)[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:20])[CH3:21]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 866945744-[5-(2-Triisopropylsilanyl-oxazol-5-yl)-furo[2,3-c]pyridin-2-yl]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 866945774-(5-Oxazol-5-yl-furo[2,3-c]pyridin-2-yl)-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride (1 mol/L in tetrahydrofuran; 1.5 mL) is added to a solution of 4-[5-(2-triisopropylsilanyl-oxazol-5-yl)-furo[2,3-c]pyridin-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (0.31 g) in tetrahydrofuran (6 mL) chilled in an ice bath. The cooling bath is removed and the solution is stirred at room temperature for 2 h. Water is added and the resulting mixture is extracted with ethyl acetate. The combined extracts are dried (Na2SO4) and concentrated. The residue is purified by HPLC on reversed phase (methanol/water) to give the title compound. LC (method 4): tR=1.66 min; Mass spectrum (ESI+): m/z=370 [M+H]+.

Workup

  1. temperaturechilled in an ice bath
  2. customThe cooling bath is removed
  3. additionWater is added
  4. extractionthe resulting mixture is extracted with ethyl acetate
  5. dry with materialThe combined extracts are dried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue is purified by HPLC on reversed phase (methanol/water)

Sources & evidence

ORD record
ord-0f5aeacbdd20497187ca1be87d47be94
Source dataset
uspto-grants-2015_04
Patent number
US09012456B2

Reaction notes

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