Methanol → HCID 53978020, compound

HRID 234768Notes

Reaction equation

HRID 234768 reaction equation
CO.[BH4-].[Li+].[Cl:5][C:6]1[CH:11]=[C:10]([C:12](OC)=[O:13])[CH:9]=[CH:8][C:7]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]1[NH:26][N:25]([C:27]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[NH:24][N:23]=1>O1CCCC1>[Cl:5][C:6]1[CH:11]=[C:10]([CH2:12][OH:13])[CH:9]=[CH:8][C:7]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]1[NH:26][N:25]([C:27]([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[NH:24][N:23]=1

Participants

5

Reactant 3

HCID 887Methanol2×HCID 4148881Lithium borohydrideHCID 54113670HCID 54113670, compound

Product 1

HCID 53978020HCID 53978020, compoundYield 98.19%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.27 g of methanol (39.6 mmol) and 1.29 g of lithium borohydride (59.4 mmol) are added to a solution of 22.0 g (39.6 mmol) of the compound from Example XXXIV in 180 ml of tetrahydrofuran, and the mixture is then stirred at room temperature for 30 minutes and under reflux for 1 hour. Addition of a further 0.63 g of methanol (0.20 mmol) and stirring under reflux for 1 hour brings the reaction to completion. The reaction mixture is concentrated; the residue is taken up in 200 ml of methylene chloride and 100 ml of 1N potassium hydrogen sulphate solution are slowly added under a vigorous stream of argon, using an ice-bath. After the phases have been separated, the aqueous phase is extracted with methylene chloride. The combined organic phases are washed with saturated sodium chloride solution, dried over sodium sulphate and concentrated, to give 20.5 g of white crystals [98.19% of theory; melting point 186°-7° C. (decomposition), Rf 0.15 (hexane:ethyl acetate=3:1)].

Workup

  1. temperatureunder reflux for 1 hour
  2. stirringstirring
  3. temperatureunder reflux for 1 hour
  4. customthe reaction to completion
  5. concentrationThe reaction mixture is concentrated
  6. addition100 ml of 1N potassium hydrogen sulphate solution are slowly added under a vigorous stream of argon
  7. customAfter the phases have been separated
  8. extractionthe aqueous phase is extracted with methylene chloride
  9. washThe combined organic phases are washed with saturated sodium chloride solution
  10. dry with materialdried over sodium sulphate
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-3393fe9dd40649d8a917a317794e446a
Source dataset
uspto-grants-1997_01
Patent number
US05596006

Reaction notes

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