Ethyl trifluoroacetate → (1S,2S,5R)-2-[(2,2,2-Trifluoro-acetylamino)-methyl]-3-aza-bicyclo[3.1.0]hexane-3-carboxylic Acid Tert-butyl Ester

HRID 560346Notes

Reaction equation

HRID 560346 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[CH2:22][C@H:21]2[C@H:19]([CH2:20]2)[C@H:18]1[CH2:23][NH2:24])=[O:16])([CH3:13])([CH3:12])[CH3:11]>C1COCC1>[C:10]([O:14][C:15]([N:17]1[CH2:22][C@H:21]2[C@H:19]([CH2:20]2)[C@H:18]1[CH2:23][NH:24][C:3](=[O:5])[C:2]([F:1])([F:8])[F:9])=[O:16])([CH3:13])([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 9794Ethyl trifluoroacetateHCID 59444330tert-butyl (1S,2S,5R)-2-(aminomethyl)-3-azabicyclo(3.1.0)hexane-3-carboxylate

Product 1

HCID 59444338(1S,2S,5R)-2-[(2,2,2-Trifluoro-acetylamino)-methyl]-3-aza-bicyclo[3.1.0]hexane-3-carboxylic Acid Tert-butyl Ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At 0° C. ethyl trifluoroacetate (41.9 mmol, 1.3 eq) is added to a solution of (1S,2S,5R)-2-Aminomethyl-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester (32.0 mmol, 1.00 eq) in THF (80 mL). The mixture is stirred at RT for 90 min and the solvents are removed in vacuo to give the desired product which is used without further purification in the next step. LC-MS: tR=0.94 min; [M+H]+=309.1.

Workup

  1. customthe solvents are removed in vacuo

Sources & evidence

ORD record
ord-364c9022e17d4fd6866794f0eb8c1a10
Source dataset
uspto-grants-2011_11
Patent number
US08063099B2

Reaction notes

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