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

HRID 278333Notes

Reaction equation

HRID 278333 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-aa0f4202aa7a4283b372a5d915a953fa
Source dataset
uspto-grants-2002_03
Patent number
US06358980B1

Reaction notes

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