HCID 21849954, compound → HCID 15435323, compound

HRID 617813Notes

Reaction equation

HRID 617813 reaction equation
Cl.[CH3:2][N:3]([CH3:28])[CH2:4][CH2:5][N:6]1[C:25](=[O:26])[C:10]2[CH:11]=[CH:12][CH:13]=[C:14]3[C:15]4[C:16]5[O:23][CH2:22][C:21](=[O:24])[C:17]=5[CH:18]=[CH:19][C:20]=4[N:8]([C:9]=23)[C:7]1=[O:27]>C(O)(=O)C>[CH3:2][N:3]([CH3:28])[CH2:4][CH2:5][N:6]1[C:25](=[O:26])[C:10]2[CH:11]=[CH:12][CH:13]=[C:14]3[C:15]4[C:16]5[O:23][CH2:22][CH:21]([OH:24])[C:17]=5[CH:18]=[CH:19][C:20]=4[N:8]([C:9]=23)[C:7]1=[O:27]

Participants

3

Reactant 1

HCID 21849954HCID 21849954, compound

Product 1

HCID 15435323HCID 15435323, compoundYield 21.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

105.5 mg (0.29 mmol) of the compound of Example 8 was dissolved in acetic acid (1 ml). Then 36 μl of an 8 M borane/pyridine complex was added thereto under stirring at room temperature. The obtained mixture was stirred for 4.5 hours. After adding 30 μl of an 8 M borane/pyridine complex thereto, the obtained mixture was further stirred overnight and concentrated. Then it was extracted by adding thereto water, a saturated aqueous solution of sodium hydrogencarbonate and chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel column chromatography. The product thus obtained was recrystallized from ethanol/diisopropyl ether to thereby give 22.6 mg of the title compound.

Workup

  1. additionThen 36 μl of an 8 M borane/pyridine complex was added
  2. stirringThe obtained mixture was stirred for 4.5 hours
  3. additionAfter adding 30 μl of an 8 M borane/pyridine complex
  4. concentrationconcentrated
  5. extractionThen it was extracted
  6. additionby adding
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography
  10. customThe product thus obtained
  11. customwas recrystallized from ethanol/diisopropyl ether

Sources & evidence

ORD record
ord-dbaca3a55cc24225a9101e2d7198c77c
Source dataset
uspto-grants-1999_09
Patent number
US05952335

Reaction notes

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