Water → HCID 67157798, compound

HRID 30172Notes

Reaction equation

HRID 30172 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:14]([C:16]1[O:17][C:18]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)=[CH:19][CH:20]=1)=O)=O)(C)(C)C.O.NN.[OH-].[K+].O>C(O)COCCO>[F:27][C:24]1[CH:23]=[CH:22][C:21]([C:18]2[O:17][C:16]([CH2:14][CH:9]3[CH2:10][CH2:11][CH2:12][CH2:13][NH:8]3)=[CH:20][CH:19]=2)=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 67158216HCID 67158216, compound

Product 1

HCID 67157798HCID 67157798, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Procedure

To a solution of (RS)-1-(tert-butyloxycarbonyl)-2-((5-(4-fluorophenyl)-furan-2-yl)carbonyl)piperidine (2.0 g, 5.36 mmol) in diethylene glycol (20 g), was added hydrazine hydrate (0.31 ml, 5.36 mmol) and the resultant mixture heated at 100° C. for 30 min. After cooling to room temperature, potassium hydroxide (1.0 g, 17.8 mmol) was added and the mixture heated at 200° C. for 18 h. The reaction mixture was then poured into water (100 ml) and extracted with diethyl ether (3×75 ml). The combined organic extracts were dried (Na2SO4) and evaporated in vacuo to give the title compound as a brown oil (0.88 g, 63%).

Workup

  1. temperaturethe mixture heated at 200° C. for 18 h
  2. extractionextracted with diethyl ether (3×75 ml)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-833207da9f374c3c903eabc45f79e847
Source dataset
uspto-grants-2008_09
Patent number
US07423052B2

Reaction notes

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