2-(Phenylmethyl)oxirane → HCID 58933661, compound

HRID 854294Notes

Reaction equation

HRID 854294 reaction equation
[CH2:1]([CH:8]1[CH2:10][O:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:11]1[CH2:16][CH2:15][CH:14]([CH2:17][NH:18][C:19]([C:21]2[CH:22]=[N:23][NH:24][CH:25]=2)=[O:20])[CH2:13][CH2:12]1>C(O)(C)C>[OH:9][CH:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:10][N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][NH:18][C:19]([C:21]2[CH:25]=[N:24][NH:23][CH:22]=2)=[O:20])[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 948262-(Phenylmethyl)oxiraneHCID 58933866HCID 58933866, compound

Product 1

HCID 58933661HCID 58933661, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-benzyloxirane (0.01 mL, 0.07 mmol) in iso-propyl alcohol (5 mL) was added 1H-pyrazole-4-carboxylic acid (piperidin-4-ylmethyl)-amide (EXAMPLE 137, Step 1) (15 mg, 0.07 mmol). The resulting reaction mixture was heated to 60° C. for 24 h. The reaction mixture was concentrated, partitioned between EtOAc and aqueous sodium bicarbonate. The organic phase was dried, the solvent evaporated, and the crude product purified by reverse phase HPLC to give 1H-Pyrazole-4-carboxylic acid [1-(2-hydroxy-3-phenyl-propyl)-piperidin-4-ylmethyl]-amide.

Workup

  1. customThe resulting reaction mixture
  2. concentrationThe reaction mixture was concentrated
  3. custompartitioned between EtOAc and aqueous sodium bicarbonate
  4. customThe organic phase was dried
  5. customthe solvent evaporated
  6. customthe crude product purified by reverse phase HPLC

Sources & evidence

ORD record
ord-f59a86fb09614aed8a2c6d7e0e4385e2
Source dataset
uspto-grants-2007_08
Patent number
US07259157B2

Reaction notes

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