Trifluoroacetic acid → 3-(2-Cyclopropylmethoxyethylidene)-8-aza-bicyclo[3.2.1]octane

HRID 1191497Notes

Reaction equation

HRID 1191497 reaction equation
C(OC([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][C:11](=[CH:16][CH2:17][O:18][CH2:19][CH:20]1[CH2:22][CH2:21]1)[CH2:12]2)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:20]1([CH2:19][O:18][CH2:17][CH:16]=[C:11]2[CH2:12][CH:13]3[NH:8][CH:9]([CH2:15][CH2:14]3)[CH2:10]2)[CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 689113073-(2-Cyclopropylmethoxyethylidene)-8-azabicyclo[3.2.1]octane-8-carboxylic acid t-butyl ester

Product 1

HCID 689104243-(2-Cyclopropylmethoxyethylidene)-8-aza-bicyclo[3.2.1]octaneYield 117.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A reaction flask was charged with 3-(2-cyclopropylmethoxyethylidene)-8-azabicyclo[3.2.1]octane-8-carboxylic acid t-butyl ester (138LH49) (0.115 g, 0.37 mmol) in DCM (2 mL). TFA (0.5 mL) was added and the reaction was stirred at rt for 3 h. The reaction mixture was quenched with 1 M NaOH and the product extracted into diethyl ether. The combined organic phases were dried over Na2SO4, filtered, and concentrated to give the crude title compound (0.090 g).

Workup

  1. customThe reaction mixture was quenched with 1 M NaOH
  2. extractionthe product extracted into diethyl ether
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0cbd23e03b7443dab75a6e5af0aeb0bd
Source dataset
uspto-grants-2014_03
Patent number
US08680115B2

Reaction notes

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