Phenylacetaldehyde → HCID 67511755, compound

HRID 2410636Notes

Reaction equation

HRID 2410636 reaction equation
N1[CH2:8][CH2:7][CH2:6][C@@H:2]1[C:3](O)=[O:4].C(N(C(C)C)C(C)C)C.[C:18]1(=[O:24])[CH2:23][CH2:22][CH2:21]C=C1.[C:25]1(CC=O)[CH:30]=[CH:29]C=[CH:27][CH:26]=1>C1(C)C=CC=CC=1>[OH:24][C@H:18]1[C@@H:23]2[CH2:22][CH2:21][C@@H:6]([CH2:2][C:3]2=[O:4])[C@@H:7]1[C:8]1[CH:29]=[CH:30][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 998PhenylacetaldehydeHCID 8988D-ProlineHCID 135942-Cyclohexen-1-oneHCID 81531Diisopropylethylamine

Product 1

HCID 67511755HCID 67511755, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
45 °C

Procedure

To a mixture of D-proline (2.93 g), N-ethyl-diisopropylamine (4.36 mL) in toluene (70 mL) was added 2-cyclohexen-1-one (10 mL) and phenyl acetaldehyde (14.6 mL) at 20-25° C. The mixture was stirred for 3 d at 45° C. IPC according to LC-MS method 1 indicated>99% conversion. The suspension was cooled to 20-25° C. and filtered. The filter cake was washed with water (3×10 mL), followed by toluene wash (3×10 mL). The filter cake was dried on the filter by sucking air through the filter. Yield: 13.2 g, 60%. 1H-NMR (CDCl3) corresponds to structure of compound ent-2. Chiral HPLC method:enantiomeric ratio=27:73 (2:ent-2), diastereomeric purity: 100%; LC-MS method 1: 100% a/a, tR=1.19.

Workup

  1. temperatureThe suspension was cooled to 20-25° C.
  2. filtrationfiltered
  3. washThe filter cake was washed with water (3×10 mL)
  4. washwash (3×10 mL)
  5. customThe filter cake was dried on the
  6. filtrationfilter

Sources & evidence

ORD record
ord-1949bc14546541deac6096462b6ff5cc
Source dataset
uspto-grants-2014_08
Patent number
US08816118B2

Reaction notes

Loading…