2-Amino-2-phenylethan-1-ol → HCID 58110194, compound

HRID 2068653Notes

Reaction equation

HRID 2068653 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:15])[CH2:9][CH2:10][CH2:11][C:12]([OH:14])=O)=[CH:4][CH:3]=1.[C:16]1([C@@H:22]([CH2:24]O)[NH2:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@:8]23[O:15][CH2:24][C@H:22]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[N:23]2[C:12](=[O:14])[CH2:11][CH2:10][CH2:9]3)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 1347972-Amino-2-phenylethan-1-olHCID 6890964-(4-Fluorobenzoyl)butyric Acid

Product 1

HCID 58110194HCID 58110194, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5-(4-Fluoro-phenyl)-5-oxo-pentanoic acid (1 g, 5.10 mmol) and (S)-(+)-2-phenylglycinol (0.839 g, 6.12 mmol) in toluene (15 mL) together with 4 Å molecular sieves was heated at 140° C. under Dean-Stark conditions for 20 hours. The reaction mixture was filtered through Celite®, evaporated and the residue dissolved in ethyl acetate then re-evaporated. The crude material was purified by column chromatography eluting with 20-40% ethyl acetate in cyclohexane to afford (3S,8aS)-8a-(4-fluoro-phenyl)-3-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-one (1.08 g).

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. customevaporated
  3. dissolutionthe residue dissolved in ethyl acetate
  4. customthen re-evaporated
  5. customThe crude material was purified by column chromatography
  6. washeluting with 20-40% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-c33561c9d35f4576ac1be843e62d210c
Source dataset
uspto-grants-2012_10
Patent number
US08299063B2

Reaction notes

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