Acetic Anhydride → HCID 86601493, compound

HRID 270129Notes

Reaction equation

HRID 270129 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

Participants

6

Reactant 3

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

Product 1

HCID 86601493HCID 86601493, compoundYield 23.8%

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 on charcoal (10%) (250 mg), N-ethyldiisopropylamine (0.941 mL), acetic anhydride (0.52 mL, 5.5 mmol) in ethyl acetate (25 mL) was hydrogenated at normal pressure for 40 min. The catalyst was filtered off and the filtrate was concentrated. The residue was purified by silica gel flash chromatography (0-60% ethyl acetate in petroleum spirit) to give the subtitled compound (155 mg).

Workup

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

Sources & evidence

ORD record
ord-edb654dc57e64f1590ae5e7f8a830bad
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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