Hydrochloric Acid → N-[(1R,3S,4S)-1-(2-Aza-bicyclo[2.2.1]hept-3-yl)methyl]-2,2,2-trifluoro-acetamide

HRID 882797Notes

Reaction equation

HRID 882797 reaction equation
Cl.C(OC([N:9]1[C@H:14]([CH2:15][NH:16][C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])[C@@H:13]2[CH2:23][C@H:10]1[CH2:11][CH2:12]2)=O)(C)(C)C>O1CCOCC1>[C@H:10]12[CH2:23][C@H:13]([CH2:12][CH2:11]1)[C@@H:14]([CH2:15][NH:16][C:17](=[O:22])[C:18]([F:20])([F:21])[F:19])[NH:9]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86649700(1R,3S,4S)-3-[(2,2,2-Trifluoro-acetylamino)-methyl]-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

Product 1

HCID 86649701N-[(1R,3S,4S)-1-(2-Aza-bicyclo[2.2.1]hept-3-yl)methyl]-2,2,2-trifluoro-acetamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of HCl in dioxane (4 M, 40 mL) is added to a solution of (1R,3S,4S)-3-[(2,2,2-trifluoro-acetylamino)-methyl]-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (12.0 mmol) in dioxane (15 mL). After 3 h the solvents are removed in vacuo to give the desired product as a brownish solid which is used without further purification in the next step. LC-MS (basic): tR=0.69 min; [M+H]+=223.2.

Workup

  1. customAfter 3 h the solvents are removed in vacuo

Sources & evidence

ORD record
ord-2b2d10562b684640a4ac4c480d97ca56
Source dataset
uspto-grants-2012_08
Patent number
US08236801B2

Reaction notes

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