Methyl iodide → HCID 71495816, compound

HRID 2171610Notes

Reaction equation

HRID 2171610 reaction equation
[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([C:11]2[C@@H:12]([O:20][CH3:21])[C@@H:13]3[CH2:18][C@@H:17](O)[CH2:16][N:14]3[N:15]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C[I:56]>C1COCC1.C(OCC)(=O)C.O>[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([C:11]2[C@@H:12]([O:20][CH3:21])[C@@H:13]3[CH2:18][C@H:17]([I:56])[CH2:16][N:14]3[N:15]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 71239416HCID 71239416, compound

Product 1

HCID 71495816HCID 71495816, compoundYield 59%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-chloro-4-((3S,3aS,5R)-5-hydroxy-3-methoxy-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazol-2-yl)-3-methylbenzonitrile obtained as in example 8 (1.0 g, 3.27 mmol) in THF (40 mL) at 0° C. were added DIAD (0.8 mL, 3.96 mmol), PPh3 (1.28 g, 4.87 mmol) and methyl Iodide (0.25 mL, 3.92 mmol) and the reaction mixture was stirred at room temperature for 24 h. Once the starting material had disappeared (monitored by TLC), reaction mixture was diluted with ethyl acetate, water and extracted. Organic layer was washed with water, brine, dried over Na2SO4 and concentrated. Purification by column chromatography (silica gel, 5% acetone in hexane) provided the title compound (0.8 g, 59%)

Workup

  1. custom(monitored by TLC), reaction mixture
  2. extractionextracted
  3. washOrganic layer was washed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customPurification by column chromatography (silica gel, 5% acetone in hexane)

Sources & evidence

ORD record
ord-e35bd5e94fd046dba9b496fefade5b6a
Source dataset
uspto-grants-2015_06
Patent number
US09051326B2

Reaction notes

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