4-Piperidone → HCID 67054566, compound

HRID 2406234Notes

Reaction equation

HRID 2406234 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.CCN(C(C)C)C(C)C.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH2:29][CH2:28][C:27]([CH3:31])([CH3:30])[CH2:26][C:25]=2[CH:32]=O)=[CH:20][CH:19]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH2:29][CH2:28][C:27]([CH3:31])([CH3:30])[CH2:26][C:25]=2[CH2:32][N:5]2[CH2:6][CH2:7][C:2](=[O:1])[CH2:3][CH2:4]2)=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 337214-PiperidoneHCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 445943302-(4-chlorophenyl)-5,5-dimethyl-1-Cyclohexene-1-carboxaldehyde

Product 1

HCID 67054566HCID 67054566, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A suspension of the hydrochloride salt of 4-oxopiperidine (273 mg, 2.01 mmol) and DIPEA (351 μL, 2.01 mmol) was stirred in DCE (9.0 mL) at room temperature for 10 minutes. 2-(4-Chlorophenyl)-5,5-dimethylcyclohex-1-enecarbaldehyde (500 mg, 2.01 mmol) was then added, followed by NaBH(OAc)3 (426 mg, 2.01 mmol) and activated molecular sieves (˜1 g). The resulting suspension was stirred at room temperature for 16 hours. The reaction mixture was then filtered through a plug of Celite, rinsing with EtOAc. The filtrate was washed sequentially with saturated aqueous NaHCO3, water, and brine. The organic layer was dried over MgSO4 and concentrated. The crude residue was purified by flash chromatography on silica gel to afford the title compound (262 mg, 40% yield). MS (ESI) m/e (M+H+): 331.88

Workup

  1. filtrationThe reaction mixture was then filtered through a plug of Celite
  2. washrinsing with EtOAc
  3. washThe filtrate was washed sequentially with saturated aqueous NaHCO3, water, and brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customThe crude residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-abb07a5dd35b4d7e9229bb558a9a620c
Source dataset
uspto-grants-2014_08
Patent number
US08809352B2

Reaction notes

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