Toluene → HCID 59732263, compound

HRID 1642469Notes

Reaction equation

HRID 1642469 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.O=[C:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1.[C-:22]#[N:23].C([Al+]CC)C.C1(C)C=CC=CC=1>ClCCCl.CCOC(C)=O.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[C:22]([C:9]1([N:5]2[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]2)[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1)#[N:23]

Participants

8

Reactant 4

HCID 1140TolueneHCID 79341Piperidin-4-olHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 16686413Diethyl aluminum cyanide

Product 1

HCID 59732263HCID 59732263, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 11026Titanium isopropoxideCatalystHCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 4-hydroxypiperidine (2.02 g, 20.0 mmol) and tert-butyl 4-oxopiperidine-1-carboxylate (3.99 g, 20.0 mmol) in 1,2-dichloroethane (50 mL) was added titanium isopropoxide (4.6 mL, 22.0 mmol) and the mixture was stirred for 18 h at room temperature. A solution of diethylaluminum cyanide in toluene (1M, 48.0 mL, 48.0 mmol) was added and stirred at room temperature for 24 h. Diluted with EtOAc and the reaction was quenched at 0° C. with saturated NaHCO3 (20 mL). The mixture was stirred a further 2 h, filtered through Celite, and the resulting filtrate was concentrated in vacuo to afford the title compound (5.89 g, 95%) as white solid, which was used for the next step without further purification.

Workup

  1. stirringstirred at room temperature for 24 h
  2. customthe reaction was quenched at 0° C. with saturated NaHCO3 (20 mL)
  3. stirringThe mixture was stirred a further 2 h
  4. filtrationfiltered through Celite
  5. concentrationthe resulting filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-7805fd289c3140569e7063409a201b9b
Source dataset
uspto-grants-2012_02
Patent number
US08119661B2

Reaction notes

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