Hydrochloric Acid → 3-Amino-2-phenylpropan-1-ol

HRID 537954Notes

Reaction equation

HRID 537954 reaction equation
[Si]([O:8][CH2:9][CH:10]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:11][N:12]1C(=O)C2C(=CC=CC=2)C1=O)(C(C)(C)C)(C)C.O.NN.Cl.C([O-])(O)=O.[Na+]>CCO>[NH2:12][CH2:11][CH:10]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:9][OH:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 516892Sodium BicarbonateHCID 69001845HCID 69001845, compound

Product 1

HCID 112865663-Amino-2-phenylpropan-1-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A cooled (0° C.) solution of 2-(3 {[tert-butyl(dimethyl)silyl]oxy}-2-phenylpropyl)-1H-isoindole-1,3(2H)-dione (0.900 g, 2.28 mmol) in EtOH (10 mL) was treated with hydrazine hydrate (1.41 mL, 3.42 mmol) and the resultant solution was allowed to warm to room temperature and stirred for 18 h. A solution of 5 N aqueous HCl in EtOH (25 mL) was added and the resulting biphasic mixture was stirred for 3 h. The mixture was treated with sat. NaHCO3, until PH=9 attained and then extracted with EtOAC (3×60 ml). The combined organic extracts were washed with brine (50 mL), dried (MgSO4), filtered and concentrated to afford the title compound as a white solid. LCMS=152.2 (M+1)+.

Workup

  1. stirringthe resulting biphasic mixture was stirred for 3 h
  2. extractionextracted with EtOAC (3×60 ml)
  3. washThe combined organic extracts were washed with brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-624c0aee670545fb84c844f55f056c33
Source dataset
uspto-grants-2014_10
Patent number
US08865707B2

Reaction notes

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