Acetic Anhydride → HCID 68817532, compound

HRID 2112735Notes

Reaction equation

HRID 2112735 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:14]([O-])=O)=[C:7]([CH:13]=1)[O:8][CH2:9][C@H:10]1[CH2:12][O:11]1.C(N(C(C)C)C(C)C)C.[C:26](OC(=O)C)(=[O:28])[CH3:27]>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH:14][C:26](=[O:28])[CH3:27])=[C:7]([O:8][CH2:9][C@H:10]2[CH2:12][O:11]2)[CH:13]=1.[OH:11][CH:10]([CH3:12])[CH2:9][O:8][C:7]1[CH:13]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=1[NH:14][C:26](=[O:28])[CH3:27]

Participants

7

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 86601492(2R)-2-[(5-Methoxy-2-nitrophenoxy)methyl]oxirane

Product 2

HCID 68817532HCID 68817532, compoundHCID 86601493HCID 86601493, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (2R)-2-[(5-methoxy-2-nitrophenoxy)methyl]oxirane (620 mg, 2.75 mmol), Pd/C (10%, 250 mg), N-ethyl-N-isopropylpropan-2-amine (0.94 mL, 5.5 mmol) and acetic anhydride (0.52 mL, 5.5 mmol) in ethyl acetate (25 mL) was hydrogenated at atmospheric pressure at room temperature for 40 minutes. The catalyst was filtered off and the filtrate was concentrated in vacuo. The residue was purified by silica gel flash chromatography (0-60% ethyl acetate in petroleum spirit) to give sub-title compound (155 mg) and 204 mg of N-[2-(2-hydroxypropoxy)-4-methoxyphenyl]acetamide (see example 14). 1H-NMR (CDCl3, 400 MHz): δ 8.22 (d, J=8.8 Hz, 1H); 7.64 (br.s, 1H); 6.55-6.49 (m, 2H); 4.34 (dd, J=2.5, 11.3 Hz, 1H); 3.94 (dd, J=6.1, 11.3 Hz, 1H); 3.78 (s, 3H); 3.39 (m, 1H); 2.96 (t, J=4.5 Hz, 1H); 2.78 (dd; J=2.6, 4.8 Hz, 1H); 2.20 (s, 3H).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by silica gel flash chromatography (0-60% ethyl acetate in petroleum spirit)

Sources & evidence

ORD record
ord-aac2509e7b50458189d4f8700332574c
Source dataset
uspto-grants-2009_04
Patent number
US07524856B2

Reaction notes

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