Ammonia → HCID 21961224, compound

HRID 2211580Notes

Reaction equation

HRID 2211580 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[S:12][CH:13]=[CH:14][C:15]=2[O:16][CH:17]2[CH:22]([OH:23])[CH:21]([OH:24])[CH:20]([OH:25])[CH:19]([CH2:26][OH:27])[O:18]2)=[O:10])=[CH:5][CH:4]=1.[BH4-].[Na+].ClCCl.CO.N>O1CCCC1.CO.O>[OH:10][CH:9]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)[C:11]1[S:12][CH:13]=[CH:14][C:15]=1[O:16][CH:17]1[CH:22]([OH:23])[CH:21]([OH:24])[CH:20]([OH:25])[CH:19]([CH2:26][OH:27])[O:18]1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 4311764Sodium borohydrideHCID 21226129Dichloromethane methanolHCID 21961225HCID 21961225, compound

Product 1

HCID 21961224HCID 21961224, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4.1 g of (4-methoxy-phenyl)-[3-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-thiophen-2-yl]-methanone were dissolved in 200 ml of tetrahydrofuran+20 ml of methanol, and 500 mg of sodium borohydride were added. After the reaction was complete (TLC check, dichloromethane/methanol/conc. ammonia=30:5:0.1; about 30-60 min), water was added and the mixture was extracted three times with ethyl acetate. The combined organic phases were dried over magnesium sulfate and concentrated. 2-{2-[Hydroxy-(4-methoxy-phenyl)-methyl]-thiophen-3-yloxy}-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol was obtained as crude product which was purified by filtration through silica gel.

Workup

  1. additionwere added
  2. additionwas added
  3. extractionthe mixture was extracted three times with ethyl acetate
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6bef190fa470400fb90e259944f6c45c
Source dataset
uspto-grants-2006_09
Patent number
US07101856B2

Reaction notes

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