Sodium borohydride → HCID 58474793, compound

HRID 1400849Notes

Reaction equation

HRID 1400849 reaction equation
[F:1][C:2]1[CH:25]=[C:24]([N+:26]([O-])=O)[CH:23]=[CH:22][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH:15]=[N:16][N:17]([CH2:19][CH:20]=[O:21])[CH:18]=3)[S:13][C:6]=12.[BH4-].[Na+]>C(Cl)Cl.CO>[NH2:26][C:24]1[CH:23]=[CH:22][C:3]([O:4][C:5]2[CH:10]=[CH:9][N:8]=[C:7]3[CH:11]=[C:12]([C:14]4[CH:15]=[N:16][N:17]([CH2:19][CH2:20][OH:21])[CH:18]=4)[S:13][C:6]=23)=[C:2]([F:1])[CH:25]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 58474435HCID 58474435, compound

Product 1

HCID 58474793HCID 58474793, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 146 (3 g, 7.53 mmol) in DCM (100 mL) and MeOH (100 mL) was added NaBH4 (0.57 g, 15.06 mmol) and the reaction mixture was stirred at 0° C. for 20 min. The mixture was quenched with saturated NH4Cl solution then extracted with DCM. The extract was collected, dried over anhydrous Na2SO4, filtered, concentrated and the residue was purified by flash column chromatography (eluent 10% MeOH in EtOAc) to afford title compound 156 (1 g, 36% yield) as white solid. MS (m/z)=371.40 (M+H).

Workup

  1. customThe mixture was quenched with saturated NH4Cl solution
  2. extractionthen extracted with DCM
  3. customThe extract was collected
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe residue was purified by flash column chromatography (eluent 10% MeOH in EtOAc)

Sources & evidence

ORD record
ord-be0e5bfd3a1342b5858a5d37ae4c9def
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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