1,2-Dichloroethane → 3-(2-Fluoro-benzylcarbamoyl)-8-aza-bicyclo[3.2.1]octane-8-carboxylic Acid Ethyl Ester

HRID 2303332Notes

Reaction equation

HRID 2303332 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH:11]2[CH2:12][CH2:13][CH:7]1[CH2:8][CH:9]([C:14]([OH:16])=O)[CH2:10]2)=[O:5])[CH3:2].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[F:31][C:32]1[CH:39]=[CH:38][CH:37]=[CH:36][C:33]=1[CH2:34][NH2:35]>Cl.CN(C=O)C.C(N(CC)CC)C>[CH2:1]([O:3][C:4]([N:6]1[CH:7]2[CH2:13][CH2:12][CH:11]1[CH2:10][CH:9]([C:14](=[O:16])[NH:35][CH2:34][C:33]1[CH:36]=[CH:37][CH:38]=[CH:39][C:32]=1[F:31])[CH2:8]2)=[O:5])[CH3:2]

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 666492-FluorobenzylamineHCID 757711-HydroxybenzotriazoleHCID 22958903HCID 22958903, compound

Product 1

HCID 229589053-(2-Fluoro-benzylcarbamoyl)-8-aza-bicyclo[3.2.1]octane-8-carboxylic Acid Ethyl EsterYield 101.9%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 100 mg of 8-aza-bicyclo[3.2.1]octane-3,8-dicarboxylic acid 8-ethyl ester, 0.056 g of HOBt, 0.074 g of EDC, 0.073 mL of triethylamine, 100 mg of 2-fluorobenzylamine and 5 mL of DMF was stirred at room temperature for 24 h, diluted with 50 mL of 1N HCl and extracted into 3×25 mL of ethyl acetate. The combined organic extracts were washed with 50 mL of saturated sodium carbonate and dried over magnesium sulfate. Removal of solvents under reduced pressure gave 150 mg of a resin.

Workup

  1. extractionextracted into 3×25 mL of ethyl acetate
  2. washThe combined organic extracts were washed with 50 mL of saturated sodium carbonate
  3. dry with materialdried over magnesium sulfate
  4. customRemoval of solvents under reduced pressure

Sources & evidence

ORD record
ord-2d6a9a9914b744bba08e127d5bf4b75a
Source dataset
uspto-grants-2002_08
Patent number
US06432976B1

Reaction notes

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