(R)-tert-butyl 3-(N-methoxy-N-methylcarbamoyl)piperidine-1-carboxylate → (R)-Tert-butyl 3-(3-chlorobenzoyl)piperidine-1-carboxylate

HRID 1254251Notes

Reaction equation

HRID 1254251 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([Mg]Cl)[CH:5]=[CH:6][CH:7]=1.CON(C)[C:13]([C@@H:15]1[CH2:20][CH2:19][CH2:18][N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16]1)=[O:14]>C1COCC1>[C:24]([O:23][C:21]([N:17]1[CH2:18][CH2:19][CH2:20][C@@H:15]([C:13](=[O:14])[C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[CH2:16]1)=[O:22])([CH3:27])([CH3:26])[CH3:25]

Participants

4

Reactant 2

HCID 30025965(R)-tert-butyl 3-(N-methoxy-N-methylcarbamoyl)piperidine-1-carboxylateHCID 178478982HCID 178478982, compound

Product 1

HCID 46831638(R)-Tert-butyl 3-(3-chlorobenzoyl)piperidine-1-carboxylateYield 132.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At −20° C., 3-chlorophenyl magnesium chloride (11 mL, 5.5 mmol, 0.5M THF solution) was added dropwise to a solution of (R)-tert-butyl 3-(N-methoxy-N-methylcarbamoyl)piperidine-1-carboxylate (500 mg, 1.84 mmol) in THF (5 mL). The solution was stirred for 2 h and allowed to warm to rt. The reaction was quenched with satd ammonium chloride solution. The aqueous layer was extracted with ether (3×). The combined organic layers were washed with brine, dried over MgSO4 and filtered. Evaporation of solvent provided (3R)-1-(tert-butoxycarbonyl)-3-(3-chlorobenzoyl)piperidine (0.79 g) as an oil that was used without purification.

Workup

  1. customThe reaction was quenched with satd ammonium chloride solution
  2. extractionThe aqueous layer was extracted with ether (3×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customEvaporation of solvent

Sources & evidence

ORD record
ord-54becb8fa964420daf4b66b3367e64f1
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

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