Allyl bromide → HCID 83206810, compound

HRID 1400725Notes

Reaction equation

HRID 1400725 reaction equation
[OH:1][C:2]1([CH3:15])[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[H-].[Na+].[CH2:18](Br)[CH:19]=[CH2:20]>CN(C=O)C>[CH2:20]([O:1][C:2]1([CH3:15])[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]1)[CH:19]=[CH2:18]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 227308121-Boc-4-methyl-piperidin-4-OL

Product 1

HCID 83206810HCID 83206810, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of tert-butyl 4-hydroxy-4-methylpiperidine-1-carboxylate (4.30 g, 20.0 mmol) in DMF (50 mL) at 0° C. was added NaH (60 wt %) (1.60 g, 39.9 mmol). The mixture was then stirred at rt for 2 h. At this time allyl bromide (8.64 mL, 100 mmol) was added slowly over the course of 5 min. The reaction mixture was stirred at rt for 3 h. It was then cooled to 0° C. and quenched with sat. NH4Cl. The reaction mixture was extracted with ether. The organic phase was dried over MgSO4, filtered and concentrated to obtain a colorless oil, which was then purified by biotage, eluting with 0-25% EtOAc/hexane to isolate 3.1 g (61%) of tert-butyl 4-(allyloxy)-4-methylpiperidine-1-carboxylate as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 6.02-5.90 (m, 1H), 5.32 (dd, J=17.2, 1.7 Hz, 1H), 5.16 (dd, J=10.4, 1.4 Hz, 1H), 3.94-3.88 (m, 2H), 3.73 (br. s., 2H), 3.19 (br. s., 2H), 1.78 (d, J=13.1 Hz, 2H), 1.53-1.42 (m, 11H), 1.21 (s, 3H).

Workup

  1. stirringThe reaction mixture was stirred at rt for 3 h
  2. temperatureIt was then cooled to 0° C.
  3. customquenched with sat. NH4Cl
  4. extractionThe reaction mixture was extracted with ether
  5. dry with materialThe organic phase was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto obtain a colorless oil, which
  9. customwas then purified by biotage
  10. washeluting with 0-25% EtOAc/hexane

Sources & evidence

ORD record
ord-b28a55efad5d4319bf0a3e721b0e48e3
Source dataset
uspto-grants-2014_12
Patent number
US08906929B2

Reaction notes

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