Sodium borohydride → HCID 86725356, compound

HRID 925247Notes

Reaction equation

HRID 925247 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:20][CH2:19][C:10]2[C:11]3[C:12](=[O:18])[CH2:13][CH2:14][C:15]=3[CH:16]=[CH:17][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2].[BH4-].[Na+]>C(O)C.O>[CH2:1]([O:3][C:4]([N:6]1[CH2:20][CH2:19][C:10]2[C:11]3[CH:12]([OH:18])[CH2:13][CH2:14][C:15]=3[CH:16]=[CH:17][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 86725303HCID 86725303, compound

Product 1

HCID 86725356HCID 86725356, compoundYield 102.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of Intermediate 3 (0.12 g, 0.37 mmol) in ethanol (2 ml) was added NaBH4 (28 gm, 0.74 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 colorless oil (104 mg) which was used as obtained in the next step. MS: ESI (positive): 276 (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-f63d422f41d24d7fbfaaf1f774388289
Source dataset
uspto-grants-2016_03
Patent number
US09284277B2

Reaction notes

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