Potassium Carbonate → HCID 53468991, compound

HRID 573804Notes

Reaction equation

HRID 573804 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:25]4[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=4)[O:19][C:20]4([CH2:24][CH2:23][CH2:22][CH2:21]4)[C:10]=3[C:9]=2[C@@H:8]([OH:35])[CH2:7][C:6]1([CH3:37])[CH3:36])(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO.O>[CH:15]([C:12]1[C:11]2[C@@H:18]([C:25]3[CH:26]=[CH:27][C:28]([C:31]([F:32])([F:34])[F:33])=[CH:29][CH:30]=3)[O:19][C:20]3([CH2:21][CH2:22][CH2:23][CH2:24]3)[C:10]=2[C:9]2[C@@H:8]([OH:35])[CH2:7][C:6]([CH3:36])([CH3:37])[C@@H:5]([OH:4])[C:14]=2[N:13]=1)([CH3:17])[CH3:16]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 66761174HCID 66761174, compound

Product 1

HCID 53468991HCID 53468991, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 887MethanolSolvent

Procedure

13 mg (3′R,6′R,9′S)-9′-hydroxy-4′-isopropyl-7′,7′-dimethyl-3′-(4-(trifluoromethyl)phenyl)-6′,7′,8′,9′-tetrahydro-3′H-spiro[cyclopentane-1,1′-furo[3,4-c]quinoline]-6′-yl acetate are dissolved in 1 ml methanol and treated with 14 mg potassium carbonate. Three drops water are added and the mixture is stirred for 3 hours at room temperature. Then the solvent is evaporated in vacuo and the residue is partitioned between water and dichloromethane. The organic phase is dried with sodium sulphate and the solvent is evaporated in vacuo. The residue is chromatographed on silica gel (hexane/ethylacetate 4:1).

Workup

  1. customThen the solvent is evaporated in vacuo
  2. customthe residue is partitioned between water and dichloromethane
  3. dry with materialThe organic phase is dried with sodium sulphate
  4. customthe solvent is evaporated in vacuo
  5. customThe residue is chromatographed on silica gel (hexane/ethylacetate 4:1)

Sources & evidence

ORD record
ord-fa1e820df69748dab8d07514024bc110
Source dataset
uspto-grants-2015_05
Patent number
US09029544B2

Reaction notes

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