Hydrochloric Acid → (2S,3R)-3-hydroxy-4-phenylbutan-2-aminium chloride

HRID 13081Notes

Reaction equation

HRID 13081 reaction equation
[ClH:1].[OH:2][C@H:3]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C@@H:4]([NH:6]C(=O)OC(C)(C)C)[CH3:5]>C(OCC)(=O)C>[Cl-:1].[OH:2][C@H:3]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C@@H:4]([NH3+:6])[CH3:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59339776tert-butyl (2S,3R)-3-hydroxy-4-phenylbutan-2-ylcarbamate

Product 1

HCID 66812618(2S,3R)-3-hydroxy-4-phenylbutan-2-aminium chloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Hydrochloric acid (5 to 6 M in isopropanol, 4 mL) was added to a solution of tert-butyl (2S,3R)-3-hydroxy-4-phenylbutan-2-ylcarbamate (640 mg, 2.41 mmol) in ethyl acetate (4 mL). The mixture was stirred at 50° C. for 2.5 h and then concentrated. The solid was dissolved in warm ethanol (4-5 mL). Diethyl ether (ca 15 mL) was added under stirring to give the subtitle compound as a light lilic precipitate (290 mg, 60%).

Workup

  1. concentrationconcentrated
  2. dissolutionThe solid was dissolved in warm ethanol (4-5 mL)
  3. additionDiethyl ether (ca 15 mL) was added
  4. stirringunder stirring

Sources & evidence

ORD record
ord-e6b5fa54e90040418c7a77518ed0288c
Source dataset
uspto-grants-2010_06
Patent number
US07728030B2

Reaction notes

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