Hydrochloric Acid → 5,6,7,8,9,10-Hexahydro-2-methyl-5,9-methanopyrido[4,3-d]azocin-1(2H)-one

HRID 272610Notes

Reaction equation

HRID 272610 reaction equation
C(OC([N:8]1[CH2:19][CH:18]2[CH2:20][CH:10]([CH2:11][C:12]3[C:13](=[O:22])[N:14]([CH3:21])[CH:15]=[CH:16][C:17]=32)[CH2:9]1)=O)(C)(C)C.Cl>C(OCC)(=O)C>[CH3:21][N:14]1[C:13](=[O:22])[C:12]2[CH2:11][CH:10]3[CH2:20][CH:18]([CH2:19][NH:8][CH2:9]3)[C:17]=2[CH:16]=[CH:15]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68807074HCID 68807074, compound

Product 1

HCID 598378495,6,7,8,9,10-Hexahydro-2-methyl-5,9-methanopyrido[4,3-d]azocin-1(2H)-oneYield 64%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 5-methyl-6-oxo-5,11-diaza-tricyclo[7.3.1.02,7]trideca-2(7),3-diene-11-carboxylic acid tert-butylester (22 mg, 0.07 mmol) (prepared above) was added anhydrous 3N HCl in ethyl acetate and the solution was stirred at room temperature for 16 h. The reaction mixture was evaporated in vacuo and the resulting white solid was recrystallized from methanol-ether to afford the desired product (9 mg, 64%). 1H NMR (CD3OD, 400 MHz) δ 7.53 (d, 1H, J=7 Hz), 6.25 (d, 1H, J=7 Hz), 3.54 (s, 3H), 3.3 (obsc. M, 4H), 3.08 (br.s, 1H), 2.85 (dd, 1H, J=19 Hz, J=7 Hz), 2.65 (d, 1H, J=19 Hz), 2.55 (br.s, 1H), 2.08 (d, 1H, J=13 Hz), 1.89 (d, 1H, J=13 Hz); APCl MS m/z 205 (M+1)+.

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customthe resulting white solid was recrystallized from methanol-ether

Sources & evidence

ORD record
ord-4953722c92e848a9b2ae8e4a0aed0115
Source dataset
uspto-grants-2008_11
Patent number
US07456177B2

Reaction notes

Loading…