Potassium Carbonate → 1-(Tert-butyl) 4-ethyl 4-({[4-(2-butynyloxy)phenyl]sulfanyl}methyl)-1,4-piperidinedicarboxylate

HRID 353551Notes

Reaction equation

HRID 353551 reaction equation
I[CH2:2][C:3]1([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.[CH2:21]([O:25][C:26]1[CH:31]=[CH:30][C:29]([SH:32])=[CH:28][CH:27]=1)[C:22]#[C:23][CH3:24].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH2:21]([O:25][C:26]1[CH:27]=[CH:28][C:29]([S:32][CH2:2][C:3]2([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]2)=[CH:30][CH:31]=1)[C:22]#[C:23][CH3:24]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 114180681-tert-Butyl 4-ethyl 4-(iodomethyl)piperidine-1,4-dicarboxylateHCID 235138844-But-2-ynyloxy-benzenethiol

Product 1

HCID 697267481-(Tert-butyl) 4-ethyl 4-({[4-(2-butynyloxy)phenyl]sulfanyl}methyl)-1,4-piperidinedicarboxylateYield 99%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.294 g (0.74 mmol) of 1-(tert-Butyl) 4-ethyl 4-(iodomethyl)piperidine-1,4-dicarboxylate, 0.145 (0.814 mmol) of 4-but-2-ynyloxy-benzenethiol and 0.204 g (1.48 mmol) of K2CO3 in 2.0 mL of DMF was stirred at room temperature for 18 h. The resulting mixture was diluted with EtOAc, washed with H2O, brine, dried over MgSO4 and concentrated in vacuo. The residue was chromatographed on silica gel eluting with EtOAc:Hexanes (1:19) to provide 0.328 g (99%) of the desired product as a colorless oil. Electrospray Mass Spec: 448.3 (M+H)+.

Workup

  1. washwashed with H2O, brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was chromatographed on silica gel eluting with EtOAc:Hexanes (1:19)

Sources & evidence

ORD record
ord-8de4e92ba49546ef8f1d589a50b89d95
Source dataset
uspto-grants-2004_06
Patent number
US06753337B2

Reaction notes

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