Hydrochloric Acid → (S)-2-amino-3-phenylpropan-1-ol hydrochloride

HRID 2396440

Reaction equation

HRID 2396440 reaction equation
C(OC([NH:8]C(C1C=CC=CC=1)(O)CC)=O)(C)(C)C.[ClH:19].[C:20]1([CH3:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[O:27]1CCO[CH2:29][CH2:28]1>>[ClH:19].[NH2:8][C@@H:29]([CH2:26][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:28][OH:27]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 312751,4-DioxaneHCID 77504178Tert-butoxycarbonylamino-1-phenyl-propan-1-ol

Product 1

HCID 69017766(S)-2-amino-3-phenylpropan-1-ol hydrochloride

Procedure

A solution of 20.10 g (80.00 mmol) of (S)-2-(tert-butoxycarbonylamino-1-phenyl-propan-1-ol [J. Med. Chem. 33, 2707 (1990)] in 200 ml of a 4N solution of gaseous hydrogen chloride in anhydrous dioxane is stirred at room temperature for 30 minutes. Thereafter, 60 ml of toluene are added and the mixture is concentrated in vacuo. This operation is repeated twice more, and the residue is then titrated with a little ether, filtered off with suction and dried under a high vacuum over KOH. 14.14 g (94% of theory) of the title compound are obtained as colourless crystals.

Workup

  1. concentrationthe mixture is concentrated in vacuo
  2. filtrationfiltered off with suction
  3. dry with materialdried under a high vacuum over KOH

Sources & evidence

ORD record
ord-8e8c2d677f86438e8cab5be150c9d721
Source dataset
uspto-grants-1996_02
Patent number
US05492896

Linked notes

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