Water → HCID 67866871, compound

HRID 1762138Notes

Reaction equation

HRID 1762138 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[C@@H:9]([OH:14])[C@H:8]([N:15]3[CH2:19][C:18](=[O:20])[CH2:17][C:16]3=[O:21])[C:7]=2[CH:22]=1)#[N:2].[BH4-].[Na+].O>CS(C)=O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[C@@H:9]([OH:14])[C@H:8]([N:15]3[CH2:19][CH:18]([OH:20])[CH2:17][C:16]3=[O:21])[C:7]=2[CH:22]=1)#[N:2]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 67867521HCID 67867521, compound

Product 1

HCID 67866871HCID 67866871, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred solution of (±)-trans-6-cyano-3,4-dihydro-2,2-dimethyl-4-(2,4-dioxo-1-pyrrolidinyl)-2H-1-benzopyran -3-ol (0. g) in dry DMSO under N2, was added NaBH4 (0.11 g). The reaction was stirred for 3 h at room temperature. Water (100 mL) was added add the aqueous phase extracted with EtOAc. The organic layer was washed with H2O add brine, dried over MgSO4, filtered and evaporated to give the crude product (0.5 g) as an orange solid. This mixture was chromatographed (chromatotron CHCl3 →CHCl3 -10% MeOH gradient elution; 2 mm silica gel) to give two fractions.

Workup

  1. additionadd the aqueous phase
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with H2O
  4. additionadd brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-370e811844904f35b244686647fe158d
Source dataset
uspto-grants-1989_05
Patent number
US04831050

Reaction notes

Loading…