Nitrogen → HCID 178449960, compound

HRID 1404403Notes

Reaction equation

HRID 1404403 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C@H:11]1[CH2:16][CH2:15][C@H:14](/[CH:17]=[N:18]/[S@@:19]([C:21]([CH3:24])([CH3:23])[CH3:22])=[O:20])[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:25]([Mg]Cl)[CH:26]=[CH2:27].N#N>C(Cl)Cl>[CH2:1]([O:8][CH2:9][CH2:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([CH:17]([NH:18][S@@:19]([C:21]([CH3:24])([CH3:23])[CH3:22])=[O:20])[CH2:27][CH:26]=[CH2:25])[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 947NitrogenHCID 178418473HCID 178418473, compoundHCID 178455588HCID 178455588, compound

Product 1

HCID 178449960HCID 178449960, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of (R,E)-N-((trans-4-(2-(benzyloxy)ethyl)cyclohexyl)methylene)-2-methylpropane-2-sulfinamide in DCM (65 mL) was added allylmagnesium chloride (2M in THF, 5.87 mL, 11.74 mmol) dropwise under N2. The resulting mixture was stirred at 0° C. for 1 h and quenched by addition of saturated NH4Cl solution, separated. The aqueous phase was extracted with EtOAc and combined organic phase were washed with brine, dried over Na2SO4. Purification by flash column chromatography (eluent: 20% EtOAc in hexanes) gave the product (2.57 g, 100%). LC/MC: 392.1 (MH)+.

Workup

  1. customquenched by addition of saturated NH4Cl solution
  2. customseparated
  3. extractionThe aqueous phase was extracted with EtOAc and combined organic phase
  4. washwere washed with brine
  5. dry with materialdried over Na2SO4
  6. customPurification by flash column chromatography (eluent: 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-68e37080acc34114989196c24b85be46
Source dataset
uspto-grants-2014_12
Patent number
US08912169B2

Reaction notes

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