Sodium borohydride → HCID 66607274, compound

HRID 1625764Notes

Reaction equation

HRID 1625764 reaction equation
[C@@H:1]1([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([CH2:19][C:20]3[S:21][C:22]([C:25]4[CH:30]=[CH:29][C:28]([CH:31]=[O:32])=[CH:27][CH:26]=4)=[CH:23][CH:24]=3)[CH:13]=2)[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3].[BH4-].[Na+]>C(O)C.O1CCCC1>[C@@H:1]1([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([CH2:19][C:20]3[S:21][C:22]([C:25]4[CH:30]=[CH:29][C:28]([CH2:31][OH:32])=[CH:27][CH:26]=4)=[CH:23][CH:24]=3)[CH:13]=2)[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 86601078HCID 86601078, compound

Product 1

HCID 66607274HCID 66607274, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-(β-D-Glucopyranosyl)-4-chloro-3-(5-(4-formylphenyl)-2-thienylmethyl)benzene (84 mg) obtained in Example 249 was dissolved in a mixture of ethanol (2 ml)-tetrahydrofuran (2 ml) and added thereto was sodium borohydride (7 mg). The mixture was stirred at room temperature for 1 hour. The mixture was quenched by 2N hydrochloric acid aqueous solution (3 drops) at 0° C., and the solvents were evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=9:1) to give the desired 1-(β-D-glucopyranosyl)-4-chloro-3-(5-(4-hydroxymethylphenyl)-2-thienylmethyl)benzene (82 mg) as colorless foam. APCI-Mass m/Z 494/496 (M+NH4).

Workup

  1. additionadded
  2. customThe mixture was quenched by 2N hydrochloric acid aqueous solution (3 drops) at 0° C.
  3. customthe solvents were evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (chloroform:methanol=9:1)

Sources & evidence

ORD record
ord-97741c498f7148929eb9b0ecca80150b
Source dataset
uspto-grants-2014_07
Patent number
US08785403B2

Reaction notes

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