Potassium Carbonate → (R)-4-Allyl-3,4,5,6-tetrahydro-1H-benzo[f][1,4]oxazocine

HRID 1429384Notes

Reaction equation

HRID 1429384 reaction equation
Br[CH2:2][C:3]1[CH:16]=[CH:15][CH:14]=[CH:13][C:4]=1[CH2:5][O:6][CH2:7][C@H:8]([NH2:12])[CH2:9][CH:10]=[CH2:11].C([O-])([O-])=O.[K+].[K+]>CCO>[CH2:9]([C@H:8]1[NH:12][CH2:2][C:3]2[CH:16]=[CH:15][CH:14]=[CH:13][C:4]=2[CH2:5][O:6][CH2:7]1)[CH:10]=[CH2:11]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 68233277(R)-1((2-(Bromomethyl)benzyl)oxy)pent-4-en-2-amine

Product 1

HCID 68233282(R)-4-Allyl-3,4,5,6-tetrahydro-1H-benzo[f][1,4]oxazocineYield 84.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of compound 18k (2.0 g, 7.0 mmol) in EtOH (20 mL) was added K2CO3 (4.8 g, 35.0 mmol) portionwise. The mixture was heated to reflux for 2 h to complete the reaction. The reaction mixture was cooled down to rt and concentrated under reduced pressure to give compound 18l (1.2 g, 84% yield), which was used without purification. LCMS (m/z): 204.1 (MH+).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 h
  3. customthe reaction
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f36a4fd96e3f441ba28d122276245a65
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

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