Methylamine → HCID 9863466, compound

HRID 741768Notes

Reaction equation

HRID 741768 reaction equation
FC(S(O[C:9]1[CH2:14][CH2:13][C:12]([C:29]#[N:30])([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)[CH:16]=2)[CH2:11][CH:10]=1)(=O)=O)(F)F.CN.[CH3:33][OH:34].CN(C)[CH:37]=[O:38]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:29]([C:12]1([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH:24]3[CH2:25][CH2:26][CH2:27][CH2:28]3)[CH:16]=2)[CH2:13][CH2:14][C:9]([C:33]([O:38][CH3:37])=[O:34])=[CH:10][CH2:11]1)#[N:30]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 9889714HCID 9889714, compoundHCID 21901440N,N-dimethylformamide methanol

Product 1

HCID 9863466HCID 9863466, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

To a solution of 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)-1cyclohexenyl trifluoromethylsulfonate (1.0 g, 2.24 mmol) in 1:1 methanol/N,N-dimethylformamide (8 mL) were added methylamine (0.66 mL, 4.72 mmol) and tetrakis(triphenylphosphine)palladium (0.13 g, 0.11 mmol). The resulting mixture was stirred at room temperature in the dark under a carbon monoxide atmosphere for 3h. The mixture was partitioned between water and ethyl acetate, the organic extract was washed three times with water, once with brine, was dried (potassium carbonate) and was evaporated.

Workup

  1. customThe mixture was partitioned between water and ethyl acetate
  2. extractionthe organic extract
  3. washwas washed three times with water
  4. dry with materialonce with brine, was dried (potassium carbonate)
  5. customwas evaporated

Sources & evidence

ORD record
ord-7a6e3fe32c7c47999e0b57add0887ed2
Source dataset
uspto-grants-1996_09
Patent number
US05552438

Reaction notes

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