8-Methyl-8-azabicyclo(3.2.1)octan-3-ol → HCID 25109111, compound

HRID 1621286Notes

Reaction equation

HRID 1621286 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[OH:32][C:33]1[CH:34]=[C:35]2[C:40](=[CH:41][CH:42]=1)[C:39](=[O:43])[NH:38][CH:37]=[CH:36]2.[CH3:44][N:45]1[CH:49]2[CH2:50][CH:51](O)[CH2:52][CH:46]1[CH2:47][CH2:48]2>C(N(CC)CC)C.ClCCl>[CH3:44][N:45]1[CH:49]2[CH2:48][CH2:47][CH:46]1[CH2:52][CH:51]([O:32][C:33]1[CH:34]=[C:35]3[C:40](=[CH:41][CH:42]=1)[C:39](=[O:43])[NH:38][CH:37]=[CH:36]3)[CH2:50]2

Participants

7

Reactant 4

HCID 84248-Methyl-8-azabicyclo(3.2.1)octan-3-ol2×HCID 11776Triphenylphosphine2×HCID 220568ethyl N-ethoxycarbonyliminocarbamate2×HCID 105111706-hydroxyisoquinolin-1(2H)-one

Product 1

HCID 25109111HCID 25109111, compoundYield 44.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

8 mL of dry dichloromethane were added to 814 mg (1.73 mmol) of polystyrene bound triphenyl phosphine. At 0° C. 234 μL (1.48 mmol) of diethyl azodicarboxylate were added. 200 mg (1.24 mmol) of 6-hydroxy-2H-isoquinolinone (66), 210 mg (1.49 mmol) of tropine and 261 μL of triethylamine were added and the reaction mixture was allowed to warm to room temperature and stirred overnight. Another 279 mg of PS-triphenyl phosphine, 43 mg of tropine, 26 μL of diethyl azodicarboxylate and 2 mL of dry dichloeomethane were added and stirring was continued overnight. The solids were filtered off and washed with THF. The mixture was evaporated and purified by flash chromatography to give 158 mg of 6-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yloxy)-2H-isoquinolin-1-one (53). Rt=0.79 min (Method B). Detected mass: 279.2 (M+H+).

Workup

  1. customAt 0° C
  2. stirringstirring
  3. waitwas continued overnight
  4. filtrationThe solids were filtered off
  5. washwashed with THF
  6. customThe mixture was evaporated
  7. custompurified by flash chromatography

Sources & evidence

ORD record
ord-c5daee6bfcea403b87481ea0384587b4
Source dataset
uspto-grants-2014_07
Patent number
US08772492B2

Reaction notes

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