Acetic Acid → HCID 77174872, compound
Reaction equation
[C:1]1(=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:7](O)(=O)[CH3:8].S([O-])([O-])(=O)=O.[Mg+2].[O:17]1[CH:22]([C:23]([OH:25])=[O:24])[CH2:21][NH:20][C:19]2[CH:26]=[CH:27][CH:28]=[CH:29][C:18]1=2.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH:1]1([N:20]2[CH2:21][CH:22]([C:23]([O:25][CH2:7][CH3:8])=[O:24])[O:17][C:18]3[CH:29]=[CH:28][CH:27]=[CH:26][C:19]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
Cyclopentanone (83 L, 0.94 mmol), acetic acid (54 L, 0.94 mmol), and magnesium sulfate (113 mg, 0.94 mmol) were added to a solution of (±)-3,4-dihydro-2H-benzo[b][1,4]oxazine-2-carboxylic acid (Example 3a, 65 mg, 0.31 mmol) in dichloroethane (1.25 mL). Sodium triacetoxyborohydride (100 mg, 0.47 mmol) was added, followed by dichloroethane (1.25 mL), and the suspension was stirred at 25° C. for 48 h. The reaction mixture was quenched with half-saturated sodium bicarbonate, and the product was extracted using 67% EtOAc/hexane (3×25 mL). The combined organic fractions were dried over sodium sulfate and concentrated. Purification of the product by flash column chromatography (10% EtOAc/hexane) afforded the title compound as an oil. MS m/z: 276 (M+1).
Workup
- customThe reaction mixture was quenched with half-saturated sodium bicarbonate
- extractionthe product was extracted
- dry with materialThe combined organic fractions were dried over sodium sulfate
- concentrationconcentrated
- customPurification of the product by flash column chromatography (10% EtOAc/hexane)
Sources & evidence
- ORD record
- ord-3326df04580f4a8882341067f04b2478
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08163766B2
Reaction notes
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