Lithium Chloride → HCID 59536731, compound

HRID 220686Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH:9]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH3:22])[CH2:10][C:11](OC)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].[Cl-].[Li+].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C(COC)OC>[OH:12][CH2:11][CH2:10][CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH3:22]

Participants

Conditions

Temperature: 85 °C

Procedure

Of the compound from Example 171A, 1.34 g (4.33 mmol) were dissolved in 10 ml of dimethoxyethane and admixed with 246 mg (6.50 mmol) of sodium borohydride and 37 mg (0.87 mmol) of lithium chloride. The mixture was heated at 85° C. for 16 h. For work-up, it was cooled to RT and cautiously admixed with 10 ml of saturated aqueous sodium potassium tartrate solution. It was extracted with three times 20 ml of ethyl acetate. The combined organic phases were dried over magnesium sulphate, filtered and freed from the solvent on a rotary evaporator. The crude product was purified by chromatography on silica gel (elution: cyclohexane/ethyl acetate 9:1, 7:3). This gave 348 mg (29% of theory) of the title compound.

Workup

temperatureFor work-up, it was cooled to RT
extractionIt was extracted with three times 20 ml of ethyl acetate
dry with materialThe combined organic phases were dried over magnesium sulphate
filtrationfiltered
customfreed from the solvent on a rotary evaporator
customThe crude product was purified by chromatography on silica gel (elution: cyclohexane/ethyl acetate 9:1, 7:3)

Sources & evidence

ORD record: ord-5e4b015857224d3495ab73ad2bf3dfaa
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202895B2

Reaction notes

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