Ethyl trifluoroacetate → (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

HRID 425799Notes

Reaction equation

HRID 425799 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]([O:5]CC)=O.[C:10]([O:14][C:15]([N:17]1[CH2:24][C@H:23]2[C@H:19]([CH2:20][CH:21]([CH3:25])[CH2:22]2)[C@H:18]1[CH2:26][NH2:27])=[O:16])([CH3:13])([CH3:12])[CH3:11]>C1COCC1>[C:10]([O:14][C:15]([N:17]1[CH2:24][C@H:23]2[C@H:19]([CH2:20][CH:21]([CH3:25])[CH2:22]2)[C@H:18]1[CH2:26][NH:27][C:3](=[O:5])[C:2]([F:1])([F:8])[F:9])=[O:16])([CH3:12])([CH3:13])[CH3:11]

Participants

4

Reactant 2

HCID 9794Ethyl trifluoroacetateHCID 59411604(1S,2S,5R)-2-aminomethyl-7-methyl-3-aza-bicyclo[3.3.0]-octane-3-carboxylic acid tert.-butyl ester

Product 1

HCID 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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl trifluoroacetate (0.7 mL, 1.4 eq) was added to a solution of (1S,2S,5R)-2-aminomethyl-7-methyl-3-aza-bicyclo[3.3.0]-octane-3-carboxylic acid tert.-butyl ester (1.1 g) in dry THF (14 mL). The reaction mixture was stirred at RT for 1 h. Solvent and excess ethyl trifluoroacetate were evaporated in vacuo. The resulting product was then used for the next step without purification

Workup

  1. customSolvent and excess ethyl trifluoroacetate were evaporated in vacuo
  2. customThe resulting product was then used for the next step without purification

Sources & evidence

ORD record
ord-8a7c1d34377e492a85e0fbc3ecbd2260
Source dataset
uspto-grants-2012_01
Patent number
US08106215B2

Reaction notes

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