Acetonitrile → HCID 86718456, compound

HRID 1396637Notes

Reaction equation

HRID 1396637 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:25]([O-:27])=[O:26])=[C:6]([CH:24]=1)[O:7][C@@H:8]1[CH2:12][O:11][C@@H:10]2[C@@H:13](OS(C(F)(F)F)(=O)=O)[CH2:14][O:15][C@H:9]12.C(#N)C>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:25]([O-:27])=[O:26])=[C:6]([CH:24]=1)[O:7][C@H:8]1[C@H:9]2[O:15][CH2:14][CH2:13][C@H:10]2[O:11][CH2:12]1

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 86718454HCID 86718454, compound

Product 1

HCID 86718456HCID 86718456, compound

Procedure

To 4.0 g (9.6 mmol) [(3R,3aR,6S,6aS)-3-(5-fluoro-2-nitro-phenoxy)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-6-yl]trifluoromethanesulfonate (intermediate III.3) in acetonitrile 1.1 g (28.8 mmol) sodium borohydride are added. The reaction mixture is stirred at RT for 10 days. The reaction mixture is evaporated, taken up in ice water, carefully acidified with aqueous 4 mol/l HCl and extracted with EtOAc. The organic phases are pooled, washed with water, dried and evaporated. The residue is purified by FC.

Workup

  1. customThe reaction mixture is evaporated
  2. extractionextracted with EtOAc
  3. washwashed with water
  4. customdried
  5. customevaporated
  6. customThe residue is purified by FC

Sources & evidence

ORD record
ord-35bd327059384c348846fd2fed69436a
Source dataset
uspto-grants-2014_12
Patent number
US08901138B2

Reaction notes

Loading…