Water → tert-butyl (3R*,4S*)-4-{[(4-chlorophenyl)carbonyl]amino}-3-(3,4-dichlorophenyl)piperidine-1-carboxylate

HRID 1260938Notes

Reaction equation

HRID 1260938 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:12][C@H:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][C@H:14]1[C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=1.C(N(CC)CC)C.[Cl:41][C:42]1[CH:50]=[CH:49][C:45]([C:46](Cl)=[O:47])=[CH:44][CH:43]=1.O>C(#N)C>[Cl:41][C:42]1[CH:50]=[CH:49][C:45]([C:46]([NH:12][C@H:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:23])[CH3:24])=[O:20])[CH2:15][C@H:14]2[C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=2)=[O:47])=[CH:44][CH:43]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 86631348HCID 86631348, compound

Product 1

HCID 86631347tert-butyl (3R*,4S*)-4-{[(4-chlorophenyl)carbonyl]amino}-3-(3,4-dichlorophenyl)piperidine-1-carboxylateYield 99%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of the compound (0.55 g) obtained in step 4 and triethylamine (439 μL) in acetonitrile (5 mL) was added 4-chlorobenzoyl chloride (177 μL) at 0° C., and the mixture was stirred at room temperature for 14 hr. The reaction mixture was poured into water, and the resultant product was extracted with ethyl acetate. The organic layer was washed with aqueous sodium hydrogen carbonate solution and brine and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 25→50% ethyl acetate/hexane) to give the title compound (0.51 g, 99%) as a white powder.

Workup

  1. extractionthe resultant product was extracted with ethyl acetate
  2. washThe organic layer was washed with aqueous sodium hydrogen carbonate solution and brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 25→50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-556895c8a521482582d13d85e50efa70
Source dataset
uspto-grants-2013_06
Patent number
US08470816B2

Reaction notes

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