HCID 15572611, compound → HCID 69697954, compound

HRID 2267604Notes

Reaction equation

HRID 2267604 reaction equation
[OH:1][CH:2]([CH:8]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N+:22]([O-])=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]>C(O)C.[Pd]>[NH2:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[O:15][CH:8]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH:2]([OH:1])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

4

Reactant 1

HCID 15572611HCID 15572611, compound

Product 1

HCID 69697954HCID 69697954, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of erythro ethyl 2-hydroxy-3-(2-nitrophenoxy)-3-phenylpropanoate (6a) (3.956 g, 11.940 mmol) in ethanol (150 mL) was added 5% palladium on carbon (500 mg) and the mixture was hydrogenated at 35 psi on a Parr shaker for 30 min. The reaction mixture was filtered through diatomaceous earth and the resulting solution concentrated in-vacuo. The residue was purified by flash chromatography on silica gel eluting with ethyl acetate to afford the title compound (3.585 g, 99%) as a red oil. 1H NMR (300 MHz, CDCl3) δ1.18 (t, 3H), 3.34 (m, 1H), 3.99 (br, 2H), 4.17 (m, 2H), 4.60 (m, 1H), 5.42 (d, 1H, J=3 Hz), 6.51-6.65 (m, 2H), 6.69-6.82 (m, 2H), 7.20-7.40 (m, 5H). MS APCI, m/z=324 (M+Na). LC/MS: 1.70 min.

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. concentrationthe resulting solution concentrated in-vacuo
  3. customThe residue was purified by flash chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-027e33b4db6d475bb8f81c83a81c583a
Source dataset
uspto-grants-2010_12
Patent number
US07858776B2

Reaction notes

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