HCID 18545188, compound → 3-(4-chlorophenyl)-8-azabicyclo[3.2.1]oct-2-ene

HRID 1266997Notes

Reaction equation

HRID 1266997 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:14][CH:13]3[N:15](C(O)=O)[CH:10]([CH2:11][CH2:12]3)[CH:9]=2)=[CH:4][CH:3]=1>C(O)(=O)C.O.[Zn]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH2:9][CH:10]3[NH:15][CH:13]([CH2:12][CH2:11]3)[CH:14]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 18545188HCID 18545188, compound

Product 1

HCID 98592793-(4-chlorophenyl)-8-azabicyclo[3.2.1]oct-2-eneYield 81.5%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Racemic 3-(4-Chloro-phenyl)-8-aza-bicyclo[3.2.1]oct-2-ene-8-carboxylic acid #2,2,2-trichloro-ethyl ester (7.5 g, 18.98 mmol) in acetic acid (75 mL) and water (10 mL) was heated at 45° C. Zinc (16.63 g, 257.39 mmol) was added portionwise to the reaction over 1 hour. Mix was filtered through Celite and the filtrate was concentrated to a clear oil. The oil was dissolved in water (100 mL) adjusted to PH=12 with 1N sodium hydroxide and extracted with ethyl acetate (2×200 mL). The combined organic layer was washed with brine (100 mL), dried with magnesium sulfate and concentrated to yield racemic 3-(4-Chloro-phenyl)-8-aza-bicyclo[3.2.1]oct-2-ene (3.4 g, 81.5%) as a white solid with had the following properties: Mp 91-93° C.; 1H NMR CDCl3 δ: 7.30-7.21 (m, 4H), 6.41 (d, J=5.6 Hz, 1H), 3.85 (t, J=5.6 Hz, 1H), 3.80 (t, J=5.6 Hzm 1H), 2.80 (d, J=17.2 Hz, 1H), 2.17 (d, J=17.2 Hz, 1H), 2.11-1.69 (m, 3H), 1.66-1.57 (m, 1H). IR (KBr): 3965, 3887, 3721, 3664, 3477, 3304, 3237, 3081, 3048, 3020, 2966, 2928, 2882, 2835, 2710, 2675, 2595, 2495, 2425, 2396, 2362, 2314, 2104, 1967, 1935, 1913, 1894, 1847, 1791, 1707, 1630, 1589, 1563, 1494, 1466, 1446, 1428, 1403, 1380, 1360, 1341, 1307, 1279, 1249, 1239, 1221, 1190, 1151, 1092, 1068, 1030, 1008, 973, 948, 935, 916, 876, 850, 811, 755, 738, 726, 706, 672, 665, 631, 610, 554, 544, 524, 519, 469, 445, 433, 421, (cm−1). Analysis calculated for C13H14ClN.⅓ H2O: C, 69.18; H, 6.55; N, 6.21; Found: C, 69.42; H, 6.36; N, 6.15.

Workup

  1. additionMix
  2. filtrationwas filtered through Celite
  3. concentrationthe filtrate was concentrated to a clear oil
  4. dissolutionThe oil was dissolved in water (100 mL)
  5. extractionextracted with ethyl acetate (2×200 mL)
  6. washThe combined organic layer was washed with brine (100 mL)
  7. dry with materialdried with magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-eefb3ea4db25498e8ed718f7ae6d4d18
Source dataset
uspto-grants-2003_04
Patent number
US06552015B2

Reaction notes

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