Hydrochloric Acid → (S)-3-methyl-1-{4-[5-(trifluoromethyl)pyridin-2-yl]phenyl}butan-1-amine

HRID 1427474Notes

Reaction equation

HRID 1427474 reaction equation
CC([S@@]([NH:7][C@H:8]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][N:20]=2)=[CH:15][CH:14]=1)[CH2:9][CH:10]([CH3:12])[CH3:11])=O)(C)C.Cl.C(OCC)C>CO>[CH3:11][CH:10]([CH3:12])[CH2:9][C@@H:8]([C:13]1[CH:14]=[CH:15][C:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:26])[F:27])=[CH:21][N:20]=2)=[CH:17][CH:18]=1)[NH2:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 67981157(S,S)-2-methyl-N-(3-methyl-1-{4-[5-(trifluoromethyl)pyridin-2-yl]phenyl}butyl)propane-2-sulfinamide

Product 1

HCID 67980909(S)-3-methyl-1-{4-[5-(trifluoromethyl)pyridin-2-yl]phenyl}butan-1-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A cooled solution (0° C. by internal thermometer) of (S,S)-2-methyl-N-(3-methyl-1-{4-[5-(trifluoromethyl)pyridin-2-yl]phenyl}butyl)propane-2-sulfinamide (74.0 g, 179 mmol) in methanol (0.90 L) was treated with 2.0M hydrochloric acid in diethylether (233 ml, 466 mmol) dropwise while maintaining the reaction temperature below 15° C. Following 1 hour, the solvent was removed in vacuo and the resulting oil was treated with diethylether to precipitate the product as a fine white solid. The solid was collected via filtration, and washed with diethylether (3×100 ml). The remaining solid was dried in vacuo. The crude material was used for further transformations.

Workup

  1. temperaturewhile maintaining the reaction temperature below 15° C
  2. customthe solvent was removed in vacuo
  3. additionthe resulting oil was treated with diethylether
  4. customto precipitate the product as a fine white solid
  5. filtrationThe solid was collected via filtration
  6. washwashed with diethylether (3×100 ml)
  7. customThe remaining solid was dried in vacuo

Sources & evidence

ORD record
ord-d423b386eb8e4d99914db53cd9ef6cee
Source dataset
uspto-grants-2015_01
Patent number
US08933104B2

Reaction notes

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