Dimethyl Sulfoxide → HCID 15928287, compound

HRID 1073087Notes

Reaction equation

HRID 1073087 reaction equation
Br[CH2:2][CH2:3][C@H:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@@H:6]([C:17]([O:19][CH3:20])=[O:18])[CH2:5]1.CS(C)=O.[C-:25]#[N:26].[Na+].O>[Cl-].[Na+].O>[C:25]([CH2:2][CH2:3][C@H:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@@H:6]([C:17]([O:19][CH3:20])=[O:18])[CH2:5]1)#[N:26]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 8929Sodium CyanideHCID 15719005HCID 15719005, compound

Product 1

HCID 15928287HCID 15928287, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 12.95 g (0.031 mol, containing triphenylphosphine oxide) of methyl cis-4-(2-bromoethyl)-N-t-butoxycarbonyl-2-piperidinecarboxylate and 40 ml of DMSO was added 2.30 g (0.047 mol) of sodium cyanide. The mixture was stirred for approximately 30 minutes at 50° C. To the mixture was added 50 ml each of water and brine and the mixture was extracted four times with methylene chloride and once with diethyl ether. The organic extracts were combined, washed twice with water and once with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The resultant residue was dissolved in 100 ml of ethyl acetate:hexane (1:3, v:v) and filtered through a one inch pad of silica gel (230-400 mesh) in a 150 ml medium porosity sintered glass funnel. The silica gel pad was washed with an additional 400 ml of ethyl acetate:hexane (1:3, v:v). The filtrate was concentrated under vacuum to afford 7.85 g of methyl cis-4-(2-cyanoethyl)-N-t-butoxycarbonyl-2-piperidinecarboxylate.

Workup

  1. extractionthe mixture was extracted four times with methylene chloride
  2. washwashed twice with water and once with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum
  5. dissolutionThe resultant residue was dissolved in 100 ml of ethyl acetate:hexane (1:3, v:v)
  6. filtrationfiltered through a one inch pad of silica gel (230-400 mesh) in a 150 ml medium porosity sintered glass funnel
  7. washThe silica gel pad was washed with an additional 400 ml of ethyl acetate:hexane (1:3, v:v)
  8. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-ba0a790c529b470f970f5dfa50d267b9
Source dataset
uspto-grants-1990_11
Patent number
US04968678

Reaction notes

Loading…