Isopropyl iodide → HCID 67071346, compound

HRID 874332Notes

Reaction equation

HRID 874332 reaction equation
[CH3:1][O:2][C:3](=[O:29])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:25](=[CH:26][CH:27]=1)[O:24][C:11]1([CH2:16][CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12]1)[CH2:10][C:9]2=[O:28].I[CH:31]([CH3:33])[CH3:32].C([O-])([O-])=O.[K+].[K+]>CC#N>[CH3:1][O:2][C:3](=[O:29])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:25](=[CH:26][CH:27]=1)[O:24][C:11]1([CH2:16][CH2:15][CH2:14][N:13]([CH:31]([CH3:33])[CH3:32])[CH2:12]1)[CH2:10][C:9]2=[O:28]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 67071461HCID 67071461, compound2×

Product 1

HCID 67071346HCID 67071346, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of (±)-(E)-3-[4-oxo-spiro(chromane-2,3′-piperidine)-6-yl]-acrylic acid methyl ester hydrochloride (Intermediate 2, 300 mg, 0.888 mmol), 2-iodopropane (302 mg, 1.76 mmol) and K2CO3 (491 mg, 3.55 mmol) in CH3CN (40 ml) was stirred at 75° C. for 24 h. The solvent was removed and the residue was partitioned between EtOAc and H2O. The organic layer was dried over Na2SO4 and evaporated to dryness. The crude mixture was purified by column chromatography (eluent: DCM/MeOH 98:2) to give (±)-(E)-3-[1′-isopropyl-4-oxo-spiro(chromane-2,3′-piperidine)-6-yl]-acrylic acid methyl ester (252 mg).

Workup

  1. customThe solvent was removed
  2. customthe residue was partitioned between EtOAc and H2O
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customevaporated to dryness
  5. customThe crude mixture was purified by column chromatography (eluent: DCM/MeOH 98:2)

Sources & evidence

ORD record
ord-5a0f6d4305994b68ba2f2ee8cf306b0b
Source dataset
uspto-grants-2015_03
Patent number
US08980877B2

Reaction notes

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