Di-tert-butyl dicarbonate → Tert-butyl 4-(4-bromophenyl)-4-methylpiperidine-1-carboxylate

HRID 1050545Notes

Reaction equation

HRID 1050545 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:14])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[O:15](C(OC(C)(C)C)=O)[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=O>C(Cl)Cl.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:14])[CH2:9][CH2:10][N:11]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:15])[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 631566114-(4-Bromophenyl)-4-methylpiperidine

Product 1

HCID 118115382Tert-butyl 4-(4-bromophenyl)-4-methylpiperidine-1-carboxylateYield 88.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(4-bromophenyl)-4-methylpiperidine (285) (4.1 g, 16 mmol) in DCM (20 mL) was added (BOC)2O (5.7 g, 26 mmol). The resulting mixture was stirred at RT for 30 min before being diluted with water (10 mL). The mixture was extracted with DCM (10 mL×2). The combine organic layers were washed with brine, dried, concentrated in vacuo, and subjected to silica flash column using 0 to 20% EtOAc in PE to give tert-butyl 4-(4-bromophenyl)-4-methylpiperidine-1-carboxylate (286) (5 g, 88%) as colorless oil.

Workup

  1. extractionThe mixture was extracted with DCM (10 mL×2)
  2. washThe combine organic layers were washed with brine
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d4521c51f0804f13845306baa3078f09
Source dataset
uspto-grants-2016_07
Patent number
US09382246B2

Reaction notes

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