Water → HCID 86662322, compound

HRID 449655Notes

Reaction equation

HRID 449655 reaction equation
C(O[C:6]([N:8]1[CH2:13][C@@H:12]2[CH2:14][C@H:9]1[CH2:10][N:11]2[CH2:15][C:16]1[CH:17]=[N:18][C:19]([Cl:22])=[CH:20][CH:21]=1)=O)(C)(C)C.O>C(O)=O.C=O>[Cl:22][C:19]1[N:18]=[CH:17][C:16]([CH2:15][N:11]2[CH2:10][C@@H:9]3[CH2:14][C@H:12]2[CH2:13][N:8]3[CH3:6])=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 962WaterHCID 86662323HCID 86662323, compound

Product 1

HCID 86662322HCID 86662322, compoundYield 61.9%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 712FormaldehydeSolvent

Conditions

Temperature
70 °C

Procedure

(1S,4S)-5-(6-Chloro-pyridin-3-ylmethyl)-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (1.1 g, 3.4 mmol) was dissolved in a mixture of 11.3 ml of formic acid and 22.6 ml of formalin. The reaction was heated at 70° C. for 4 hours, and then cooled to room temperature. Water was added and the aqueous layer was extracted with DCM. The aqueous layer was carefully basified with solid potassium carbonate and extracted 3 times with DCM. The crude product was purified by chromatography using a gradient of 5% to 25% methanol in DCM. Ammonium hydroxide (approximately 2%) had been added to the methanol. 500 mg of a colorless liquid was obtained (61.9%).

Workup

  1. temperaturecooled to room temperature
  2. extractionthe aqueous layer was extracted with DCM
  3. extractionextracted 3 times with DCM
  4. customThe crude product was purified by chromatography
  5. additionAmmonium hydroxide (approximately 2%) had been added to the methanol

Sources & evidence

ORD record
ord-1d0b55c4d6ce46e08bf9e7640c9255c3
Source dataset
uspto-grants-2013_07
Patent number
US08481540B2

Reaction notes

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