Hydrochloric Acid → (2S)-1-Phenylbut-3-en-2-amine--hydrogen chloride (1/1)

HRID 2380009Notes

Reaction equation

HRID 2380009 reaction equation
C(OC([NH:8][CH:9](C1C=CC=CC=1)[CH2:10][CH:11]=C)=O)(C)(C)C.[ClH:19].[C:20]1([CH3:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O1CCOCC1>[ClH:19].[NH2:8][C@H:9]([CH:10]=[CH2:11])[CH2:26][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 15087930HCID 15087930, compound

Product 1

HCID 45594315(2S)-1-Phenylbut-3-en-2-amine--hydrogen chloride (1/1)

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 5.00 g (20.21 mmol) of (S)-2-(tert-butoxycarbonylamino-1-phenylbut-3-ene [J. R. Luly et al., J. Org. Chem. 52, 1487 (1987)] in 100 ml of a 4N solution of gaseous hydrogen chloride in anhydrous dioxane was stirred at room temperature for 30 min. 15 ml of toluene were then added and the mixture was concentrated in vacuo. This process was repeated twice more, then the residue was triturated with a little ether, filtered off with suction and dried in a high vacuum over KOH. 3.69 g (99% of theory) of the title compound were obtained as colourless crystals.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customthe residue was triturated with a little ether
  3. filtrationfiltered off with suction
  4. dry with materialdried in a high vacuum over KOH

Sources & evidence

ORD record
ord-0b93c61e2a5242009bf7d454da0816cf
Source dataset
uspto-grants-1994_11
Patent number
US05364931

Reaction notes

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