Water → cis-2-Benzyl-1,3,4,5,5a,6,7,11b-octahydro-3-oxo-2H-naphth[1,2-c]azepine

HRID 6402Notes

Reaction equation

HRID 6402 reaction equation
[O:1]=[C:2]1[NH:8][CH2:7][C@H:6]2[C:9]3[C:14]([CH2:15][CH2:16][C@H:5]2[CH2:4][CH2:3]1)=[CH:13][CH:12]=[CH:11][CH:10]=3.CC(C)([O-])C.[K+].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O>C1COCC1>[CH2:23]([N:8]1[C:2](=[O:1])[CH2:3][CH2:4][C@@H:5]2[CH2:16][CH2:15][C:14]3[C:9]([C@@H:6]2[CH2:7]1)=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 23665647Potassium tert-butoxideHCID 67854163cis-1,3,4,5,5a,6,7,11b-octahydro-3-oxo-2H-naphth[1,2-c]azepine

Product 1

HCID 67854162cis-2-Benzyl-1,3,4,5,5a,6,7,11b-octahydro-3-oxo-2H-naphth[1,2-c]azepineYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of cis-1,3,4,5,5a,6,7,11b-octahydro-3-oxo-2H-naphth[1,2-c]azepine (1.0 g, 4.65 mmol), from Step 3 of Example 75, in 20 mL of dry THF, was added potassium t-butoxide (0.78 g, 6.9 mmol). The reaction mixture was stirred at ambient temperature for 0.5 h and then cooled to 0° C. and benzyl bromide (0.8 mL, 6.7 mmol) was added. The reaction mixture was allowed to warm to ambient temperature, stirred for 3 h and then poured into water and extracted three times with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was crystalized from ether/hexane to afford 1.1 g (79% yield) of the title compound, m.p. 114°-115° C.; MS DCl--NH3M/Z: 306 (M+H)+ ; 1H NMR (CDCl3) δ1.5-2.2 (5H, m), 2.42-2.54 (1H, m), 2.58-3.03 (5H, m), 3.79 (1H, dd, J=9.5, 13.6 Hz), 4.44 (1H, d, J=13.6 Hz), 4.95 (1H, d, J=13.6 Hz), 6.47-6.5 (1H, m), 6.97-7.45 (8H, m).

Workup

  1. temperaturecooled to 0° C.
  2. temperatureto warm to ambient temperature
  3. stirringstirred for 3 h
  4. extractionextracted three times with ethyl acetate
  5. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was crystalized from ether/hexane

Sources & evidence

ORD record
ord-43574d7d6f5f4aa8866fdde3b5c2f0dc
Source dataset
uspto-grants-1993_09
Patent number
US05248677

Reaction notes

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