HCID 86671485, compound → HCID 68312943, compound

HRID 1530719Notes

Reaction equation

HRID 1530719 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][C@@H:13]([CH:17]([NH:25][CH2:26][CH:27]=[CH2:28])[CH2:18][CH2:19]OS(C)(=O)=O)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CC#N>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][C@@H:13]([CH:17]2[CH2:18][CH2:19][N:25]2[CH2:26][CH:27]=[CH2:28])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 86671485HCID 86671485, compound

Product 1

HCID 68312943HCID 68312943, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (R)-3-(1-allylamino-3-methanesulfonyloxypropyl)piperidine-1-carboxylic acid benzyl ester (326 mg, 0.794 mmol) in CH3CN (12 mL) was heated at 100° C. for 1 h using microwave irradiation. After cooling to RT, the reaction mixture was concentrated in vacuo. The residue was partitioned between 2M sodium carbonate and EtOAc. The aqueous phase was extracted with EtOAc. The combined organic phases were washed with brine, then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si-PCC, gradient 2-5% 2M NH3/MeOH in DCM) affording the title compound (0.2127 g, 85%, 2 steps) as a colourless gum. LCMS (Method B): RT 2.03 min [M+H]+ 315.

Workup

  1. custommicrowave irradiation
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customThe residue was partitioned between 2M sodium carbonate and EtOAc
  4. extractionThe aqueous phase was extracted with EtOAc
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was purified by column chromatography (Si-PCC, gradient 2-5% 2M NH3/MeOH in DCM)

Sources & evidence

ORD record
ord-d570a105e88f44e29bda078353f9d8a6
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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