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

HRID 263847Notes

Reaction equation

HRID 263847 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 min. After that, 60 ml of toluene are added and the mixture is concentrated in vacuo. This procedure is repeated a further two times and the residue is then triturated with a little ether, filtered off with suction and dried under 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. customthe residue is then triturated with a little ether
  3. filtrationfiltered off with suction
  4. dry with materialdried under high vacuum over KOH

Sources & evidence

ORD record
ord-ab4decc95fcb469fbf128d77222c7e65
Source dataset
uspto-grants-1997_07
Patent number
US05646121

Reaction notes

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