HCID 86657390, compound → HCID 58424856, compound

HRID 2409430Notes

Reaction equation

HRID 2409430 reaction equation
[CH3:1][O:2][CH2:3][N:4]1[C:13]2[CH:14]=[CH:15][C:16]([CH2:18]C(=O)C)=[CH:17][C:12]=2[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]1=[O:22].[O:23]1CC[CH2:25][CH2:24]1.CSC.B>O1CCCC1>[OH:23][CH2:24][CH2:25][CH2:18][C:16]1[CH:15]=[CH:14][C:13]2[N:4]([CH2:3][O:2][CH3:1])[C:5](=[O:22])[C:6]3[CH:7]=[CH:8][CH:9]=[N:10][C:11]=3[C:12]=2[CH:17]=1

Participants

4

Reactant 2

HCID 86657390HCID 86657390, compoundHCID 178419155HCID 178419155, compound

Product 1

HCID 58424856HCID 58424856, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound (780 mg, 2.50 mmol) prepared in step 5 was dissolved in tetrahydrofuran, added dropwise with 2 M borane dimethyl sulfide tetrahydrofuran solution (6.24 ml, 12.49 mmol). The resulting mixture was stirred for 3 hours at room temperature and extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and concentrated to dryness. The residue was then purified by flash column chromatography (chloroform:methanol=15:1) to obtain title compound (45 mg, yield: 75%, white solid).

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated to dryness
  4. customThe residue was then purified by flash column chromatography (chloroform:methanol=15:1)

Sources & evidence

ORD record
ord-d097813b1c2c46d29bdc60effa04c388
Source dataset
uspto-grants-2014_08
Patent number
US08815891B2

Reaction notes

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