Hydrochloric Acid → HCID 14856370, compound

HRID 1089554Notes

Reaction equation

HRID 1089554 reaction equation
[O:1]1[C:9]2[CH:10]=[CH:11][C:12]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])=[CH:13][C:8]=2[O:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:19]1(=O)[CH2:23][CH2:22][CH2:21][CH2:20]1.[BH3-]C#N.[Na+].Cl>CO>[CH:19]1([N:4]2[CH2:3][CH2:2][O:1][C:9]3[CH:10]=[CH:11][C:12]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])=[CH:13][C:8]=3[O:7][CH2:6][CH2:5]2)[CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 8452CyclopentanoneHCID 5003444Sodium cyanoborohydrideHCID 14856361HCID 14856361, compound

Product 1

HCID 14856370HCID 14856370, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To methanol add N-(3,4,5,6-tetrahydro-2H-1,7,4-benzodioxazonin-9-yl)methanesulfonamide, cyclopentanone, and NaBH3CN. Adjust the pH to six with concentrated HCl. Monitor the progress of the reaction by thin-layer chromatography. Upon completion add concentrated HCl until gas evolution ceases. Partition the reaction mixture between EtOAc and water. Add 1N aqueous NaOH until the solution is basic. Separate and dry the organic layer over Na2SO4. Filter the drying agent and remove the solvent in vacuo to obtain the title compound.

Workup

  1. customMonitor the progress of the reaction by thin-layer chromatography
  2. customPartition the reaction mixture between EtOAc and water
  3. additionAdd 1N aqueous NaOH until the solution
  4. customSeparate
  5. dry with materialdry the organic layer over Na2SO4
  6. filtrationFilter the drying agent
  7. customremove the solvent in vacuo

Sources & evidence

ORD record
ord-40ec62ea468e4a849c10ed0da0a50288
Source dataset
uspto-grants-1990_10
Patent number
US04966967

Reaction notes

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