Water → (1R,9aR)-1-(4-Nitrophenoxymethyl)octahydroquinolizine

HRID 1695521Notes

Reaction equation

HRID 1695521 reaction equation
[C@H:1]1([CH2:11][OH:12])[C@@H:10]2[N:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1.[H-].[Na+].F[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1.O>CN(C=O)C>[N+:22]([C:19]1[CH:20]=[CH:21][C:16]([O:12][CH2:11][C@H:1]2[C@@H:10]3[N:5]([CH2:6][CH2:7][CH2:8][CH2:9]3)[CH2:4][CH2:3][CH2:2]2)=[CH:17][CH:18]=1)([O-:24])=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 91461(-)-LUPININE

Product 1

HCID 67276527(1R,9aR)-1-(4-Nitrophenoxymethyl)octahydroquinolizine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(1R,9aR)-1-(Octahydroquinolizin-1-yl)methanol (2.5 g) was added to a suspension of sodium hydride (60% in oil, 710 mg) in DMF (20 ml) and, after gas evolution ceased, 4-fluoronitrobenzene (2.51 g) was added. After 2 hours, the reaction mixture was hydrolyzed with water and then partitioned between ethyl acetate and dilute hydrochloric acid. The aqueous phase was made alkaline with sodium hydroxide solution and extracted twice with ethyl acetate. The two ethyl acetate phases were combined, dried over magnesium sulfate and concentrated. The product with the molecular weight of 290.37 (C16H22N2O3); MS (ESI): 291 (M+H+) was obtained in this way.

Workup

  1. custompartitioned between ethyl acetate and dilute hydrochloric acid
  2. extractionextracted twice with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customMS (ESI): 291 (M+H+) was obtained in this way

Sources & evidence

ORD record
ord-f1767e8cd21842cf9198eeb0cc375503
Source dataset
uspto-grants-2012_04
Patent number
US08163741B2

Reaction notes

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