Sodium borohydride → HCID 86725345, compound

HRID 925238Notes

Reaction equation

HRID 925238 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:27][CH2:26][C:15]2=[CH:16][CH:17]=[C:18]3[C:22]([C:21](=[O:23])[C:20]([F:25])([F:24])[CH2:19]3)=[C:14]2[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C.O>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][C:14]2[C:22]3[CH:21]([OH:23])[C:20]([F:24])([F:25])[CH2:19][C:18]=3[CH:17]=[CH:16][C:15]=2[CH2:26][CH2:27]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 86725344HCID 86725344, compound

Product 1

HCID 86725345HCID 86725345, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of the product from step (b) (0.18 g, 0.49 mmol) dissolved in ethanol (2 ml) was added NaBH4 (0.046, 1.21 mmol). The reaction mixture was allowed to stir at RT for 1 hour. The reaction mixture was diluted with water and extracted with DCM (3×). The combined DCM extracts were washed with brine, dried (Na2SO4), and solvent evaporated in vacuo to give the sub-titled compound as a white semi-solid (0.13 g) which was used as obtained in the next step. MS: ESI (positive): 374 (M+H).

Workup

  1. extractionextracted with DCM (3×)
  2. washThe combined DCM extracts were washed with brine
  3. dry with materialdried (Na2SO4), and solvent
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-c77a2c65e2b74c1080b1196eb9a715ab
Source dataset
uspto-grants-2016_03
Patent number
US09284277B2

Reaction notes

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