Hydrazine hydrate (1:1) → HCID 71060155, compound

HRID 1036711Notes

Reaction equation

HRID 1036711 reaction equation
C([O:3][C:4]([C:6]1([C:19](=O)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]1)=O)C.O.[NH2:28][NH2:29]>CCO>[C:15]([O:14][C:12]([N:8]1[CH2:9][CH2:10][CH2:11][C:6]2([C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:29][NH:28][C:4]2=[O:3])[CH2:7]1)=[O:13])([CH3:18])([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 71060365HCID 71060365, compound

Product 1

HCID 71060155HCID 71060155, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of racemic mixture of 3-benzoyl-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (step 1) (400 mg, 1.1 mmol) in EtOH (4 ml) was added hydrazine hydrate (166 mg, 3.3 mmol). The reaction mixture was stirred at RT for 30 min before heating in the microwave at 120° C. for 3 hours. The reaction mixture was concentrated in vacuo, dissolved in EtOAc (10 ml) and washed with brine (20 ml). The aqueous phase was further washed with EtOAc (10 ml). The organics portions were combined, dried (MgSO4) and concentrated in vacuo. Purification of the crude product by chromatography on silica eluting with 0-60% EtOAc in iso-hexane afforded the title compound.

Workup

  1. temperaturebefore heating in the microwave at 120° C. for 3 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutiondissolved in EtOAc (10 ml)
  4. washwashed with brine (20 ml)
  5. washThe aqueous phase was further washed with EtOAc (10 ml)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customPurification of the crude product by chromatography on silica eluting with 0-60% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-2173f439485b41b2877ba93b90be43ed
Source dataset
uspto-grants-2013_10
Patent number
US08546416B2

Reaction notes

Loading…