Methanol → HCID 18004948, compound

HRID 428579Notes

Reaction equation

HRID 428579 reaction equation
[CH3:1][S:2][CH:3]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:5]2([CH2:10][CH2:9][N:8]([C:11]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:16][CH:15]=3)=[O:12])[CH2:7][CH2:6]2)[CH2:4]1.[Na].C[OH:34]>C1COCC1.O>[CH3:1][S:2]([CH:3]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:5]2([CH2:10][CH2:9][N:8]([C:11]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)=[CH:16][CH:15]=3)=[O:12])[CH2:7][CH2:6]2)[CH2:4]1)=[O:34]

Participants

6

Reactant 3

HCID 887MethanolHCID 5360545SodiumHCID 18004925HCID 18004925, compound

Product 1

HCID 18004948HCID 18004948, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,3-dihydro-1-methylthio-N-4-biphenylylspiro[1H-indene-3,4′-piperidine]-1′-carboxamide (1100, 55.4 mg, 0.129 mmol) in methanol (3.0 mL), THF (2.0 mL) and H2O (1.0 mL) was added sodium meta periodade (34.6 mg, 0.161 mmol). After being stirred for 35 h at room temperature, the resulting mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried (Na2SO4), and concentrated in vacuo. The residue was triturated with ethyl acetate and isopropyl ether to give 2,3-dihydro-1-methylsulfinyl-N-4-biphenylylspiro[1H-indene-3,4′-piperidine]-1′-carboxamide 45.4 mg; 79%) as an amorphous solid, 1200.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with ethyl acetate and isopropyl ether

Sources & evidence

ORD record
ord-16dbe9511c34450c8f5628032393e5c9
Source dataset
uspto-grants-2001_11
Patent number
US06313298B1

Reaction notes

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