Sodium borohydride → HCID 68448458, compound

HRID 2233193Notes

Reaction equation

HRID 2233193 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6](=[O:12])[N:5]3[CH2:13][C:14]([OH:19])([C:15](OC)=[O:16])[C:3]=1[C:4]=23.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:11]=[CH:10][C:9]2[NH:8][CH2:7][C:6](=[O:12])[N:5]3[CH2:13][C:14]([OH:19])([CH2:15][OH:16])[C:3]=1[C:4]=23

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 68448048HCID 68448048, compound

Product 1

HCID 68448458HCID 68448458, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 7-fluoro-6-hydroxy-3-oxo-5,6-dihydro-3H-pyrrolo[1,2,3-de]quinoxaline-6-carboxylate (0.558 g, 0.002 mol) in methanol (40 mL) was cooled to 0° C. and treated with sodium borohydride (0.080 g, 0.002 mol). After 2 hours and again after a further 2 hours, further portions of sodium borohydride (0.04 g, 0.5 equivalent each time) were added at 0° C. After 5 hours in total, the reaction mixture was quenched by addition of water (2 mL) and the solvent was removed. The residue was placed directly onto the top of a 20 g silica gel column and chromatographed, eluting with a 0-100% ethyl acetate in hexane gradient, then with a 0-50% methanol in ethyl acetate gradient to afford the product (0.331 g, 66%).

Workup

  1. waitagain after a further 2 hours
  2. customAfter 5 hours in total, the reaction mixture was quenched by addition of water (2 mL)
  3. customthe solvent was removed
  4. customchromatographed
  5. washeluting with a 0-100% ethyl acetate in hexane gradient

Sources & evidence

ORD record
ord-5040fea7216a47ff91309657023d2687
Source dataset
uspto-grants-2010_05
Patent number
US07709483B2

Reaction notes

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