Ammonia → HCID 21961224, compound

HRID 1445326Notes

Reaction equation

HRID 1445326 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 actetate. 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 actetate
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2c7d0838b17a4862b1f77dd3cc03a241
Source dataset
uspto-grants-2010_02
Patent number
US07666848B2

Reaction notes

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