Acetic Acid → HCID 21362442, compound

HRID 497493Notes

Reaction equation

HRID 497493 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][C@@H:7]2[CH2:12][CH2:11][CH2:10][N:9]([C:13]([C@@H:15]3[CH2:20][CH2:19][O:18][CH2:17][C@H:16]3[NH2:21])=O)[CH2:8]2)=[CH:4][CH:3]=1.O1CCCC1.C(O)(=O)C>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C@@H:7]2[CH2:12][CH2:11][CH2:10][N:9]([CH2:13][C@@H:15]3[CH2:20][CH2:19][O:18][CH2:17][C@H:16]3[NH2:21])[CH2:8]2)=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 69748357HCID 69748357, compound

Product 1

HCID 21362442HCID 21362442, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

[(S)-3-(4-Fluoro-benzyl)-piperidin-1-yl]-[(3S,4R)-3-aminotetrahydro-pyran-4-yl]-methanone (367 mg, 1.14 mmol) was treated with borane-tetrahydrofuran complex in tetrahydrofuran (1.0 M; 46 mL, 46 mmol) and stirred for 20 h. The mixture was treated slowly with 20% acetic acid in methanol (25 mL), and the resulting mixture was stirred at room temperature for 3 h. The solvents were removed, and the residue was dissolved in water, made basic (pH 11) with 50% sodium hydroxide, and extracted with dichloromethane. The combined organic phases were dried (Na2SO4) and concentrated to provide a gum (313 mg). A portion of this material (175 mg) was purified by flash column chromatography (5% methanol/dichloromethane, containing 0.5% ammonium hydroxide) to provide the product (103 mg, 52%) as an oil which solidified on standing.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 3 h
  2. customThe solvents were removed
  3. dissolutionthe residue was dissolved in water
  4. extractionextracted with dichloromethane
  5. dry with materialThe combined organic phases were dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-54e4fb6de3154b5baef64f43a29c6533
Source dataset
uspto-grants-2005_09
Patent number
US06949546B2

Reaction notes

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