Trifluoroacetic acid → 3-Piperidin-4-ylprop-2-ynyl methanesulfonate;2,2,2-trifluoroacetic acid

HRID 1063372Notes

Reaction equation

HRID 1063372 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]#[C:15][CH2:16][O:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH2:10][CH2:9]1)=O)(C)(C)C.[C:22]([OH:28])([C:24]([F:27])([F:26])[F:25])=[O:23]>C(Cl)Cl>[F:25][C:24]([F:27])([F:26])[C:22]([OH:28])=[O:23].[NH:8]1[CH2:9][CH2:10][CH:11]([C:14]#[C:15][CH2:16][O:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 865852774-(3-Methanesulfonyloxy-prop-1-ynyl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 865852783-Piperidin-4-ylprop-2-ynyl methanesulfonate;2,2,2-trifluoroacetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2.96 g (9.4 mmol) of 4-(3-Methanesulfonyloxy-prop-1-ynyl)-piperidine-1-carboxylic acid tert-butyl ester in 50 ml CH2Cl2 was treated at 0° C. with 25.2 ml of TFA (for 20 min). After 30 min at this temperature, the reaction was evaporated, evaporated again with toluene (4 times) and dried to give 3.6 g (quantitative) of methanesulfonic acid 3-piperidin-4-yl-prop-2-ynyl ester; compound with trifluoro-acetic acid, MS: 218 (MH+).

Workup

  1. customthe reaction was evaporated
  2. customevaporated again with toluene (4 times)
  3. customdried

Sources & evidence

ORD record
ord-7e03f128aa5c49228053fc0c3e17dcc5
Source dataset
uspto-grants-2005_11
Patent number
US06964974B2

Reaction notes

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