Water → HCID 19873417, compound

HRID 466372Notes

Reaction equation

HRID 466372 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([N:15]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=O)=[CH:8][CH:7]=1)(=[O:4])=[O:3].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+].O>O1CCCC1>[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][CH2:13][N:15]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:10][CH:11]=1)(=[O:3])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 9855836Potassium sodium tartarateHCID 19873407HCID 19873407, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19873417HCID 19873417, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The amide, Hexahydro-1-[4-(methylsulfonylamino)phenylacetyl]-1H-azepine from Preparation 21 (2.8 g, 9.03 mmol) is reduced with 1.1 g of lithium aluminum hydride in 100 ml of tetrahydrofuran for 2 days at room temperature. The suspension is cooled; a saturated solution of sodium potassium tartrate is carefully added and then water. The solids are filtered and washed with tetrahydrofuran. The combined filtrates are evaporated. The residue is suspended in sodium bicarbonate and extracted with methylene chloride. The organic layer is washed with water, dried and evaporated. The residue is chromatographed on silica gel eluting 10% methanol-0.5% ammonium hydroxide-methylene chloride to yield the title compound, an oil. The MS had M/Z 296 (M+).

Workup

  1. temperatureThe suspension is cooled
  2. filtrationThe solids are filtered
  3. washwashed with tetrahydrofuran
  4. customThe combined filtrates are evaporated
  5. extractionextracted with methylene chloride
  6. washThe organic layer is washed with water
  7. customdried
  8. customevaporated
  9. customThe residue is chromatographed on silica gel eluting 10% methanol-0.5% ammonium hydroxide-methylene chloride

Sources & evidence

ORD record
ord-85ff8674fa3546f8bbfc3dcb7bf3f1c6
Source dataset
uspto-grants-1992_10
Patent number
US05155268

Reaction notes

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