Acetic Acid → (S)-tert-butyl 3-(piperidin-1-ylmethyl)piperidine-1-carboxylate
Reaction equation
[CH:1]([C@@H:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1)=O.[NH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O>>[N:16]1([CH2:1][C@@H:3]2[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1Participants
5
Procedure
To a solution of (R)-tert-butyl 3-formylpiperidine-1-carboxylate (110 mg, 0.51 mmol) and piperidine (53 mg, 0.62 mmol) was added NaBH(OAc)3 (153 mg, 0.73 mmol) and AcOH (37.2 mg, 35 μL, 0.62 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 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 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-53f92eb41b0c4956bad0f45be106e104
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08119692B2
Reaction notes
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