Pyridine → HCID 66652089, compound

HRID 1751061Notes

Reaction equation

HRID 1751061 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3([CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[C:11](=[O:18])[NH:10][CH2:9]2)=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27]>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3([CH2:13][CH2:14][N:15]([C:26]([O:28][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[O:27])[CH2:16][CH2:17]3)[C:11](=[O:18])[NH:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 10387Benzyl chloroformateHCID 939151-(4-Fluorophenyl)-1,3,8-triazaspiro(4.5)decan-4-one

Product 1

HCID 66652089HCID 66652089, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-(4-fluorophenyl)-1,3,8-triazaspiro[4.5]decan-4-one (2 g, 8.02 mmol) in dichloromethane (30 mL) and pyridine (1.3 mL, 16.04 mmol, d=0.978), was added benzyl chloroformate (1.17 mL, 8.18 mmol, d=1.195). After stirring at room temperature for 24 hours, the reaction mixture was diluted with dichloromethane (100 mL), washed with dilute citric acid, water and brine. The organic phase was dried over MgSO4, filtered and concentrated to obtain benzyl 1-(4-fluorophenyl)-4-oxo-1,3,8-triazaspiro[4.5]decane-8-carboxylate (2.12 g).

Workup

  1. washwashed with dilute citric acid, water and brine
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4b205b5bc75f49cbaca80a398993e325
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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