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

HRID 1986830Notes

Reaction equation

HRID 1986830 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-70651f507b63428299fa4aafd67114ff
Source dataset
uspto-grants-2009_06
Patent number
US07550459B2

Reaction notes

Loading…