Sodium borohydride → 2-azido-4-fluoro-2,3-dihydro-1H-inden-1-ol

HRID 646719Notes

Reaction equation

HRID 646719 reaction equation
[N:1]([CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[F:13])[C:5]1=[O:14])=[N+:2]=[N-:3].[BH4-].[Na+]>CO>[N:1]([CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[F:13])[CH:5]1[OH:14])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 866078392-azido-4-fluoro-2,3-dihydro-1H-inden-1-one

Product 1

HCID 866078402-azido-4-fluoro-2,3-dihydro-1H-inden-1-olYield 73.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-azido-4-fluoro-2,3-dihydro-1H-inden-1-one (0.81 g, 4.5 mmol) in MeOH (15.0 mL), was added NaBH4 (0.19 g, 4.5 mmol) in one portion. After stirring for 10 min at r.t., the solution was concentrated in vacuo. The residue was taken up in EtOAc (100 mL), and this solution was washed with saturated NaHCO3 (aq) (50 mL), dried (Na2SO4), filtered and concentrated in vacuo to give 0.64 g (73% yield) of 2-azido-4-fluoro-2,3-dihydro-1H-inden-1-ol as a white solid, which was used without further purification: 1H NMR (400 MHz, CDCl3): 7.23 (m, 2H), 6.97 (t, 1H), 5.15 (dd, 1H), 4.37 (q, 1H), 3.17 (d, 1H), 2.40 (d, 1H).

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. washthis solution was washed with saturated NaHCO3 (aq) (50 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f76325c72d084f60a290a5af2a2e94c6
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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