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Hydrochloric Acid → N-[(1S,2S,5R)-1-(3-Aza-bicyclo[3.1.0]hex-2-yl)methyl]-2,2,2-trifluoro-acetamide

HRID 560347
Notes
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Reaction equation

HRID 560347 reaction equation
Cl.C(OC([N:9]1[CH2:14][C@H:13]2[C@H:11]([CH2:12]2)[C@H:10]1[CH2:15][NH:16][C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])=O)(C)(C)C>O1CCOCC1>[C@H:11]12[CH2:12][C@H:13]1[CH2:14][NH:9][C@@H:10]2[CH2:15][NH:16][C:17](=[O:22])[C:18]([F:19])([F:21])[F:20]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59444338(1S,2S,5R)-2-[(2,2,2-Trifluoro-acetylamino)-methyl]-3-aza-bicyclo[3.1.0]hexane-3-carboxylic Acid Tert-butyl Ester

Product 1

HCID 59444331N-[(1S,2S,5R)-1-(3-Aza-bicyclo[3.1.0]hex-2-yl)methyl]-2,2,2-trifluoro-acetamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
45 °C

Procedure

A solution of HCl in dioxane (4 M, 30 mL) is added to a solution of (1S,2S,5R)-2-[(2,2,2-Trifluoro-acetylamino)-methyl]-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester (31.6 mmol) in dioxane (30 mL) and the mixture is stirred for 60 min at RT and for 30 min at 45° C. The solvents are removed in vacuo and the obtained solid is washed twice with a small volume of dioxane to give the desired product which is used without further purification in the next step.

Workup

  1. customThe solvents are removed in vacuo
  2. washthe obtained solid is washed twice with a small volume of dioxane

Sources & evidence

ORD record
ord-6bf5cfe467884a00a87c4f33d09aab49
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08063099B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes