Methanol → HCID 66726072, compound

HRID 1042144Notes

Reaction equation

HRID 1042144 reaction equation
C([O:3][C:4](=O)[CH2:5][CH:6]1[S:10][C:9]([C:11]2[NH:12][C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([O:20][C:21]2[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][CH:22]=2)=[CH:15][C:14]=3[O:31][CH:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)=[N:8][CH2:7]1)C.[BH4-].[Li+].O.CO>O1CCCC1.CCCCCC.C(OCC)(=O)C>[CH3:30][S:27]([C:24]1[CH:23]=[CH:22][C:21]([O:20][C:16]2[CH:17]=[C:18]3[C:13](=[C:14]([O:31][CH:32]4[CH2:37][CH2:36][O:35][CH2:34][CH2:33]4)[CH:15]=2)[NH:12][C:11]([C:9]2[S:10][CH:6]([CH2:5][CH2:4][OH:3])[CH2:7][N:8]=2)=[CH:19]3)=[CH:26][CH:25]=1)(=[O:29])=[O:28]

Participants

8

Reactant 4

HCID 887MethanolHCID 962WaterHCID 4148881Lithium borohydride3×HCID 68090840HCID 68090840, compound

Product 1

HCID 66726072HCID 66726072, compoundYield 54.1%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl(2-{5-[4-(methylsulfonyl)phenoxy]-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetate (300 mg) was dissolved in tetrahydrofuran (10 mL), lithium tetrahydroborate (29 mg) was added under ice-cooling, and the mixture was stirred at 50° C. for 30 min. To the reaction solution was added lithium tetrahydroborate (29 mg), and the mixture was stirred at 50° C. for 2.5 hr. Furthermore, lithium tetrahydroborate (29 mg) was added, and the mixture was stirred at 50° C. for 3 hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (methanol:ethyl acetate:hexane=0:90:10 to 10:90:0, volume ratio) to give the title compound (150 mg, yield 54%) as a pale-yellow amorphous solid. The amorphous solid was crystallized from ethyl acetate-diethyl ether-hexane, and the obtained crystals were recrystallized from ethyl acetate-hexane to give the title compound as pale-yellow crystals.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at 50° C. for 2.5 hr
  3. stirringthe mixture was stirred at 50° C. for 3 hr
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained crude product

Sources & evidence

ORD record
ord-61bc882f12574d4db22752cd218c195d
Source dataset
uspto-grants-2013_10
Patent number
US08557805B2

Reaction notes

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