Potassium Carbonate → HCID 53466879, compound

HRID 573806Notes

Reaction equation

HRID 573806 reaction equation
C([O:4][C@@H:5]1[C:14]2[N:13]=[C:12]([CH:15]([CH3:17])[CH3:16])[C:11]3[C@@H:18]([C:26]4[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][C:27]=4[F:36])[O:19][C:20]4([CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)[C:10]=3[C:9]=2[C@@H:8]([O:37][Si](C(C)(C)C)(C)C)[CH2:7][C:6]1([CH3:46])[CH3:45])(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO>[F:36][C:27]1[CH:28]=[C:29]([C:32]([F:33])([F:34])[F:35])[CH:30]=[CH:31][C:26]=1[C@@H:18]1[C:11]2[C:12]([CH:15]([CH3:17])[CH3:16])=[N:13][C:14]3[C@@H:5]([OH:4])[C:6]([CH3:45])([CH3:46])[CH2:7][C@H:8]([OH:37])[C:9]=3[C:10]=2[C:20]2([CH2:21][CH2:22][O:23][CH2:24][CH2:25]2)[O:19]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 66762419HCID 66762419, compound

Product 1

HCID 53466879HCID 53466879, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

17 mg (3S,6S,9S)-9-(tert-butyldimethylsilyloxy)-3-(2-fluoro-4-(trifluoromethyl)phenyl)-4-isopropyl-7,7-dimethyl-2′,3′,5′,6,6′,7,8,9-octahydro-3H-spiro[furo[3,4-c]quinoline-1,4′-pyran]-6-yl acetate are dissolved in 2 ml methanol and treated with 70 mg potassium carbonate. The mixture is stirred for 36 hours. Then the solvent is evaporated in vacuo. The residue is partitioned between water and diethylether. The organic phase is separated and dried with magnesium sulphate. The solvent is evaporated in vacuo and the residue is taken up in 1 ml tetrahydrofurane. 50 μl Tetrabutylammonium fluoride are added and the mixture is stirred for 3 hours at room temperature. The solvent is evaporated in vacuo and the residue is chromatographed on silica gel (n-hexane/ethylacetate 80:20).

Workup

  1. customThen the solvent is evaporated in vacuo
  2. customThe residue is partitioned between water and diethylether
  3. customThe organic phase is separated
  4. dry with materialdried with magnesium sulphate
  5. customThe solvent is evaporated in vacuo
  6. addition50 μl Tetrabutylammonium fluoride are added
  7. stirringthe mixture is stirred for 3 hours at room temperature
  8. customThe solvent is evaporated in vacuo
  9. customthe residue is chromatographed on silica gel (n-hexane/ethylacetate 80:20)

Sources & evidence

ORD record
ord-084240b4a3ec46d983b3c7f6ff54d0a9
Source dataset
uspto-grants-2015_05
Patent number
US09029544B2

Reaction notes

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