Methanol → HCID 14498273, compound

HRID 231073Notes

Reaction equation

HRID 231073 reaction equation
[C:1]([NH:4][CH:5]1[CH2:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[O:8][CH:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:6]1)(=[O:3])[CH3:2].[BH4-].[Na+].C[OH:25]>>[C:1]([NH:4][CH:5]1[CH:11]([OH:25])[C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[O:8][CH:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 20034453HCID 20034453, compound

Product 1

HCID 14498273HCID 14498273, compoundYield 28%

Procedure

797 mg (2.70 m moles) of 4-acetamido-2-phenyl-2,3,4,5-tetrahydro-1-benzoxepin (compound R3a of Reference Example) was dissolved in 50% methanol, 411 mg (10.8 m moles) of sodium borohydride was added to the solution at -50° C. to -20° C., and the whole was stirred for 5 hours. The reaction mixture was concentrated, and ice water was added to the concentrate. The mixture was extracted with methylene chloride, and the extract was washed with water and dried with anhydrous magnesium sulfate. After filtrating off the magnesium sulfate, the filtrate was concentrated to obtain a residue, which was then applied to a silica gel column, and eluted with a mixture of methylene chloride/methanol (98:2) to obtain stereoisomers R4a (22.5 mg; yield 28.0%) and R4b (485 mg; yield 60.4%) of the desired compound.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionice water was added to the concentrate
  3. extractionThe mixture was extracted with methylene chloride
  4. washthe extract was washed with water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. filtrationAfter filtrating off the magnesium sulfate
  7. concentrationthe filtrate was concentrated
  8. customto obtain a residue, which
  9. washeluted with a mixture of methylene chloride/methanol (98:2)

Sources & evidence

ORD record
ord-583ab322d23c48bc81c64b2e11a9b4fc
Source dataset
uspto-grants-1989_07
Patent number
US04845094

Reaction notes

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