Water → 2-Phenylprolinol

HRID 53666Notes

Reaction equation

HRID 53666 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl.[C:8]1([C@@:14]2([C:19](O)=[O:20])[CH2:18][CH2:17][CH2:16][NH:15]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+]>C(OCC)(=O)C>[C:8]1([C@@:14]2([CH2:19][OH:20])[CH2:18][CH2:17][CH2:16][NH:15]2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22872003HCID 22872003, compound

Product 1

HCID 228720042-Phenylprolinol

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Lithium aluminium hydride (1M in tetrahydrofuran; 10.6 ml) was added to a cooled (0° C.) suspension of (±)-2-phenylproline hydrochloride (0.85 g) and the mixture heated at reflux for 1.5 h. After cooling to 0° C., water (1 ml) was added followed by 2M NaOH (1 ml) and water (2 ml). The reaction mixture was diluted with ethyl acetate (50 ml) then filtered through a pad of Hi-flo and the residue concentrated in vacuo to give (±)-2-phenylprolinol as a yellow oil which solidified on standing. 1H NMR (250 MHz, CDCl3) d 7.42-7.20 (5H, m, ArH), 3.60 (1H, d, J=10.0 Hz, CHHOH), 3.49 (1H, d, J=10.0 Hz, CHHOH), 3.07 (2H, t, J=5.7 Hz, CH2N), 2.43 (2H, br s, OH and NH), 2.19-1.75 (4H, m).

Workup

  1. temperaturea cooled
  2. temperaturethe mixture heated
  3. temperatureat reflux for 1.5 h
  4. filtrationthen filtered through a pad of Hi-flo
  5. concentrationthe residue concentrated in vacuo

Sources & evidence

ORD record
ord-88421fc982a646c0adbeadb69f16a027
Source dataset
uspto-grants-1997_04
Patent number
US05620989

Reaction notes

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