Potassium Carbonate → HCID 86586716, compound

HRID 2088179Notes

Reaction equation

HRID 2088179 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([CH2:13][O:14][C@@H:15]2[CH2:21][CH2:20][C@@H:19]3[NH:22][C@@:16]2([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:17][C@H:18]3[CH:23]=O)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[C:33](=O)([O-])[O-].[K+].[K+].[N+](=C(P(=O)(OC)OC)C(=O)C)=[N-]>CO>[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[C:5]([CH2:13][O:14][C@@H:15]2[CH2:21][CH2:20][C@@H:19]3[NH:22][C@@:16]2([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:17][C@@H:18]3[C:23]#[CH:33])[CH:4]=[C:3]([C:2]([F:32])([F:1])[F:31])[CH:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 86586684HCID 86586684, compoundHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 86586716HCID 86586716, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(1R*,2R*,5S*,6R*)-2-{(3,5-Bis(trifluoromethyl)phenyl]methoxy}-6-formyl-1-phenyl-8-azabicyclo[3.2.1]octane (Example 47; 165 mg, 0.3 mmol) in methanol (3 ml) at 0° C. was treated with potassium carbonate (83 mg, 0.6 mmol) and dimethyl 1-diazo-2-oxopropylphosphonate (81 mg, 0.5 mmol) and stirred for 18 hours at room temperature. The reaction mixture was concentrated in vacuo. The residue was partitioned between water and hexane. The organics were collected, dried (MgSO4), filtered and concentrated in vacuo to afford the title compound as a white crystalline solid (123 mg, 75%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was partitioned between water and hexane
  3. customThe organics were collected
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2cf004ee93e9454e80cc47b390260353
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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