Acetic Acid → HCID 59568822, compound
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([O:23][CH3:24])[CH2:9][C@H:10]([CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[C:11]([O:13][CH3:14])=[O:12])=[CH:4][CH:3]=1.[F:25][C:26]1[CH:33]=[CH:32][C:29]([CH:30]=O)=[CH:28][C:27]=1[CH3:34].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O>>[F:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30][N:20]2[CH2:19][CH2:18][N:17]([CH2:16][CH2:15][C@@H:10]([CH2:9][C@H:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[O:23][CH3:24])[C:11]([O:13][CH3:14])=[O:12])[CH2:22][CH2:21]2)=[CH:28][C:27]=1[CH3:34]Participants
5
Procedure
To a solution of (2S,4R)-methyl 4-(4-fluorophenyl)-4-methoxy-2-(2-(piperazin-1-yl)ethyl)butanoate (62 mg, 0.11 mmol) and 4-Fluoro-3-methyl-benzaldehyde (19.3 mg, 0.14 mmol) was added NaBH(OAc)3 (32.5 mg, 0.15 mmol) and AcOH (6.6 mg, 6 μL, 0.11 mmol) at room temperature. The mixture was stirred for 8 h at the room temperature. The reaction was quenched by pouring into 20 mL 5% aqueous NaOH and diluted with ethylacetate. The mixture was extracted with more ethyl acetate (3×15 mL) and the combined organic layers washed with brine (2×10 mL) and dried over Na2SO4. The mixture was concentrated under reduced pressure and the crude product was used directly in the next reaction without further purification.
Workup
- customThe reaction was quenched
- additionby pouring into 20 mL 5% aqueous NaOH
- additiondiluted with ethylacetate
- extractionThe mixture was extracted with more ethyl acetate (3×15 mL)
- washthe combined organic layers washed with brine (2×10 mL)
- dry with materialdried over Na2SO4
- concentrationThe mixture was concentrated under reduced pressure
- customthe crude product was used directly in the next reaction without further purification
Sources & evidence
- ORD record
- ord-1c7c0314c8d5476385e23a5fbadd9b00
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08119692B2
Reaction notes
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