Formic Acid → (R)-N-[5-(2-Bromo-1-hydroxyethyl)-2-(phenylmethoxy)phenyl]formamide
Reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([OH:18])[CH2:16][Br:17])=[CH:11][C:10]=1[N+:19]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22](OC(=O)C)(=[O:24])C.C(O)=O>C1COCC1.C1(C)C=CC=CC=1.O=[Pt]=O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([OH:18])[CH2:16][Br:17])=[CH:11][C:10]=1[NH:19][CH:22]=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
(R)-1-[4-(Benzyloxy)-3-nitrophenyl]-2-bromoethanol (0.2 g, 5.7 mmol) in THF:toluene (1:1, 5 mL) was reacted with PtO2 (1% w/w) on a Parr shaker at 45 psi at rt overnight. The next morning the PtO2 was removed by filtration over celite. The filtered solution was cooled to 0° C. and a solution of acetic anhydride (0.161 mL, 0.569 mmol) and formic acid (0.043 mL, 1.140 mmol) was added dropwise to a stirred solution. After 30 min the reaction was warmed to rt and stirred for 2 h. The reaction mixture was concentrated to near dryness and water was added. The aqueous layer was extracted with EtOAc (3×25 mL). The combined organic layers were washed with NaHCO3, brine, dried over Na2SO4 (s), and concentrated. Chromatography (1:1 Hexanes/EtOAc) gave the title compound (156 mg, 78% 2 steps). ES/MS calcd. C16H17BrNO3+ 350.0. Found m/z=350 (M+H)+.
Workup
- customThe next morning the PtO2 was removed by filtration over celite
- temperatureAfter 30 min the reaction was warmed to rt
- concentrationThe reaction mixture was concentrated
- additionwas added
- extractionThe aqueous layer was extracted with EtOAc (3×25 mL)
- washThe combined organic layers were washed with NaHCO3, brine
- dry with materialdried over Na2SO4 (s)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-e11386aaa2244592965e1b3130e3e815
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08394829B2
Reaction notes
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