(Dimethyl sulfide)trihydroboron → 4-[3-Nitro-5-(trifluoromethyl)benzyl]morpholine
Reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]([C:9]2[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[C:11]([N+:19]([O-:21])=[O:20])[CH:10]=2)=O)[CH2:3][CH2:2]1.CSC.B>C1COCC1>[N+:19]([C:11]1[CH:10]=[C:9]([CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=1)[CH2:7][N:4]1[CH2:3][CH2:2][O:1][CH2:6][CH2:5]1)([O-:21])=[O:20]Participants
Procedure
In a round bottomed flask morpholino(3-nitro-5-(trifluoromethyl)phenyl)methanone (1.60 g, 5.25 mmol) was dissolved in 8 mL of anhydrous THF and cooled to 0 C. To this solution, a 2 M solution of Borane-dimethyl sulfide (10.5 mL, 21 mmol) in THF was added dropwise. The reaction was stirred overnight while warming to room temperature. The solution was then concentrated to an oil. This was partitioned between dichloromethane and water, then basified with 1 M sodium hydroxide solution, and extracted twice. The extracts were combined, washed with water and brine. They were then dried over magnesium sulfate, filtered and concentrated and purified by silica gel chromatography (using a 0-50% ethyl acetate/hexane gradient) to afford 4-(3-nitro-5-trifluoromethyl-benzyl)-morpholine (409 mg, 27% yield). 1H NMR (DMSO-d6) δ 8.46 (s, 1H), 8.4 (s, 1H), 8.15 (s, 1H), 3.7 (s, 2H), 3.6 (m, 4H), 2.4 (s, 4H).
Workup
- temperaturecooled to 0 C
- concentrationThe solution was then concentrated to an oil
- customThis was partitioned between dichloromethane and water
- extractionextracted twice
- washwashed with water and brine
- dry with materialThey were then dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- custompurified by silica gel chromatography (
Sources & evidence
- ORD record
- ord-85a26f2d4f724833b0bb876a5dca07dc
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08969587B2
Reaction notes
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