Cyclohexanone → benzyl 3-(5-amino-4-cyclohex-1-enyl-1-methyl-1H-pyrazol-3-yl)pyrrolidine-1-carboxylate

HRID 1034958Notes

Reaction equation

HRID 1034958 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH:8]2[CH2:12][CH2:11][N:10]([C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:14])[CH2:9]2)[CH:3]=1.[C:23]1(=O)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>C(O)(=O)C>[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH:8]2[CH2:12][CH2:11][N:10]([C:13]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[O:14])[CH2:9]2)[C:3]=1[C:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]=1

Participants

4

Reactant 2

HCID 7967CyclohexanoneHCID 69162082benzyl 3-(5-amino-1-methyl-1H-pyrazol-3-yl)-pyrrolidine-1-carboxylate

Product 1

HCID 69162390benzyl 3-(5-amino-4-cyclohex-1-enyl-1-methyl-1H-pyrazol-3-yl)pyrrolidine-1-carboxylateYield 53%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of EXAMPLE 24C (1.78 g, 5.92 mmol) and cyclohexanone (1.23 mL, 11.85 mmol) in acetic acid (10 mL) was stirred at ambient temperature overnight and at 55° C. for 1 day. The acetic acid was removed and the residue partitioned between sodium bicarbonate solution and ethyl acetate. The organic phase was washed with water, concentrated and the residue purified by flash chromatography on silica gel using 70-90% ethyl acetate in hexane to provide the title compound as a light yellow solid (1.19 g, 53%). MS (DCI): m/z 381 (M+H)+.

Workup

  1. customThe acetic acid was removed
  2. customthe residue partitioned between sodium bicarbonate solution and ethyl acetate
  3. washThe organic phase was washed with water
  4. concentrationconcentrated
  5. customthe residue purified by flash chromatography on silica gel using 70-90% ethyl acetate in hexane

Sources & evidence

ORD record
ord-524120b59ee94e51a667fd2808e326fb
Source dataset
uspto-grants-2013_10
Patent number
US08546368B2

Reaction notes

Loading…