Bromobenzene → HCID 21258218, compound

HRID 635217Notes

Reaction equation

HRID 635217 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C:10](=[O:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Mg].[Cl-].[NH4+]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([OH:14])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 7961BromobenzeneHCID 25517Ammonium ChlorideHCID 2756825Tert-butyl 3-oxopiperidine-1-carboxylateHCID 5462224Magnesium

Product 1

HCID 21258218HCID 21258218, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5.00 g of N-t-butoxycarbonyl-3-oxopiperidine in 10 ml of tetrahydrofuran was added dropwise under ice-cooling to a Grignard reagent solution prepared from 4.73 g of bromobenzene and 0.79 g of magnesium in 50 ml of tetrahydrofuran. The mixture was stirred at room temperature for 1 hour, followed by cooling with ice, and 100 ml of a saturated aqueous solution of ammonium chloride was added thereto dropwise. The reaction mixture was extracted with ethyl acetate, and the extract was washed successively with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The desiccant was filtered off, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=3/1) to give 4.21 g of N-t-butoxycarbonyl-3-hydroxy-3-phenylpiperidine.

Workup

  1. additionwas added
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washthe extract was washed successively with a saturated aqueous solution of sodium hydrogencarbonate
  4. dry with materiala saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate
  5. filtrationThe desiccant was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-5ceec948b38d4cde8b3ea00605235f7f
Source dataset
uspto-grants-2001_02
Patent number
US06187781B1

Reaction notes

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