Hydrochloric Acid → HCID 57779818, compound

HRID 552905Notes

Reaction equation

HRID 552905 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:14][C:13](=[O:15])[CH2:12][CH:11]3[O:16][C:17](=[O:19])[CH:18]=[C:10]23)=[CH:4][CH:3]=1.[BH4-].[Na+].Cl>CO>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:14][CH:13]([OH:15])[CH2:12][CH:11]3[O:16][C:17](=[O:19])[CH:18]=[C:10]23)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 57779832HCID 57779832, compound

Product 1

HCID 57779818HCID 57779818, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

560 mg (1.61 mmol) of 4-[(6-chloropyridin-3-yl)methyl]-6-oxo-5,6,7,7a-tetrahydrofuro[3,2-b]-pyridin-2(4H)-one (Ex. 1-14) are dissolved in 14 ml of methanol, and 45 mg (1.20 mmol) of sodium borohydride are added at 0° C. The reaction mixture is stirred at 0° C. for one hour. After addition of 7.2 ml of 5% strength hydrochloric acid, the mixture is extracted with ethyl acetate. The organic phase is dried over sodium sulphate and concentrated under reduced pressure. Purification of the residue by column chromatography on silica gel (silica gel 60, Merck, particle size: 0.04 to 0.063 mm) using the solvent mixture dichloromethane:methanol (95:5) gives both possible diastereomers of 4-[(6-chloropyridin-3-yl)methyl]-6-hydroxy-5,6,7,7a-tetrahydrofuro-[3,2-b]pyridin-2(4H)-one: (a) 152 mg (34% of theory) of diastereomer A and (b) 63 mg (11% of theory) of diastereomer B.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. dry with materialThe organic phase is dried over sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customPurification of the residue by column chromatography on silica gel (silica gel 60, Merck, particle size: 0.04 to 0.063 mm)

Sources & evidence

ORD record
ord-2df1d23300054021817847e94ae7fd15
Source dataset
uspto-grants-2011_05
Patent number
US07951951B2

Reaction notes

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