Sodium borohydride → HCID 18512008, compound

HRID 1370806Notes

Reaction equation

HRID 1370806 reaction equation
[CH2:1]([N:8]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:9]1[C:10]([CH:20]=[O:21])=[C:11]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[CH2:22]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]1[C:10]([CH2:20][OH:21])=[C:11]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH:12]=[CH:13][CH:14]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 18512376HCID 18512376, compound

Product 1

HCID 18512008HCID 18512008, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from Example 42A (0.017 g, 0.043 mmoles) in ethanol (2 mL) was treated with sodium borohydride (0.002 g, 0.053 mmoles). After stirring two hours at room temperature, the reaction mixture was quenched with saturated ammonium chloride and extracted with chloroform. The extracts were combined, dried with sodium sulfate, filtered and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, 30% ethyl acetate/hexanes) to provide the title compound (0.015 g, 88%). 1H NMR (300 MHz, CDCl3) δ7.63 (s, 1H), 7.12-7.38 (m, 13H), 4.67 (s, 2H), 4.06 (s, 4H), 2.85 (s, 3H); MS (ESI+) m/z 397 (M+H)+.

Workup

  1. customthe reaction mixture was quenched with saturated ammonium chloride
  2. extractionextracted with chloroform
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (silica gel, 30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-4798d60a619140798fdd6dbc884082d1
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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