Trifluoroacetic acid → N-[(1S,2S,5R)-7-methyl-3-aza-bicyclo[3.3.0]oct-2-ylmethyl]-2,2,2-trifluoro-acetamide

HRID 425800Notes

Reaction equation

HRID 425800 reaction equation
C(OC([N:8]1[CH2:15][C@H:14]2[C@H:10]([CH2:11][CH:12]([CH3:16])[CH2:13]2)[C@H:9]1[CH2:17][NH:18][C:19](=[O:24])[C:20]([F:23])([F:22])[F:21])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:16][CH:12]1[CH2:11][C@H:10]2[C@H:14]([CH2:15][NH:8][C@@H:9]2[CH2:17][NH:18][C:19](=[O:24])[C:20]([F:23])([F:21])[F:22])[CH2:13]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86643543(1S,2S,5R)-2-[(2,2,2-trifluoro-acetylamino)-methyl]-7-methyl-3-aza-bicyclo[3.3.0]-octane-3-carboxylic acid tert.-butyl ester

Product 1

HCID 86643544N-[(1S,2S,5R)-7-methyl-3-aza-bicyclo[3.3.0]oct-2-ylmethyl]-2,2,2-trifluoro-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold (0° C.) solution of (1S,2S,5R)-2-[(2,2,2-trifluoro-acetylamino)-methyl]-7-methyl-3-aza-bicyclo[3.3.0]-octane-3-carboxylic acid tert.-butyl ester (1.51 g) in DCM (13 mL) was slowly added TFA (3.31 mL, 10 eq). The reaction mixture was allowed to warm at RT and stirred overnight. Solvent and excess of TFA were removed in vacuo and the product was used for the next step without further purification.

Workup

  1. customSolvent and excess of TFA were removed in vacuo
  2. customthe product was used for the next step without further purification

Sources & evidence

ORD record
ord-09f31d8d967e47e9a5c4fb78cc1b43ed
Source dataset
uspto-grants-2012_01
Patent number
US08106215B2

Reaction notes

Loading…