Sodium borohydride → HCID 58081124, compound

HRID 2361749Notes

Reaction equation

HRID 2361749 reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:5]2[N:6]([CH:10]3[CH2:15][CH2:14][C:13](=[O:16])[CH2:12][CH2:11]3)[CH2:7][CH2:8][O:9][C:4]=2[CH:3]=1.[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:18]=[CH:17][C:5]2[N:6]([CH:10]3[CH2:11][CH2:12][CH:13]([OH:16])[CH2:14][CH2:15]3)[CH2:7][CH2:8][O:9][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58081149HCID 58081149, compound

Product 1

HCID 58081124HCID 58081124, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of intermediate D25 (1.3 g, 4.191 mmol) and sodium borohydride (0.476 g, 12.573 mmol) in MeOH (15 ml) was stirred at room temperature for 3 h. Then, the resulting mixture was carefully quenched with NH4Cl (aqueous sat. solution) and extracted with DCM. The organic layer was separated, dried (Na2SO4), and evaporated in vacuo. The residue was triturated with a mixture of diisopropylether/diethylether to yield D26 (1.045 g, 63%) as cis/trans mixture of isomers (34% and 66% respectively)

Workup

  1. customThen, the resulting mixture was carefully quenched with NH4Cl (aqueous sat. solution)
  2. extractionextracted with DCM
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo
  6. customThe residue was triturated with a mixture of diisopropylether/diethylether

Sources & evidence

ORD record
ord-cc825c0462ba41de944675a8b2ed1b0b
Source dataset
uspto-grants-2014_04
Patent number
US08691813B2

Reaction notes

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