Hydrochloric Acid → (+/-)-3,4-Dihydro-1'-[2-(benzofurazan-5-yl)ethyl]-6-methanesulfonamido-spiro[(2H)-1-benzopyran-2,4'-piperidine]-4-ol hydrochloride

HRID 1781422Notes

Reaction equation

HRID 1781422 reaction equation
[BH4-].[Na+].[N:3]1[O:7][N:6]=[C:5]2[CH:8]=[C:9]([CH2:12][CH2:13][N:14]3[CH2:19][CH2:18][C:17]4([CH2:24][C:23](=[O:25])[C:22]5[CH:26]=[C:27]([NH:30][S:31]([CH3:34])(=[O:33])=[O:32])[CH:28]=[CH:29][C:21]=5[O:20]4)[CH2:16][CH2:15]3)[CH:10]=[CH:11][C:4]=12.C(=O)([O-])O.[Na+].[ClH:40]>C(O)C.C(OCC)(=O)C>[ClH:40].[N:3]1[O:7][N:6]=[C:5]2[CH:8]=[C:9]([CH2:12][CH2:13][N:14]3[CH2:19][CH2:18][C:17]4([CH2:24][CH:23]([OH:25])[C:22]5[CH:26]=[C:27]([NH:30][S:31]([CH3:34])(=[O:32])=[O:33])[CH:28]=[CH:29][C:21]=5[O:20]4)[CH2:16][CH2:15]3)[CH:10]=[CH:11][C:4]=12

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1600233,4-Dihydro-1'-(2-(benzofurazan-5-yl)ethyl)-6-methanesulfonamidospiro((2H)-1-benzopyran-2,4'-piperidin)-4-oneHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydride

Product 1

HCID 19045531(+/-)-3,4-Dihydro-1'-[2-(benzofurazan-5-yl)ethyl]-6-methanesulfonamido-spiro[(2H)-1-benzopyran-2,4'-piperidine]-4-ol hydrochlorideYield 65%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium borohydride (7.5 mg, 0.2 mmol) was added to a stirred suspension of 3,4-dihydro-1'-[2-(benzofurazan-5-yl)ethyl]-6-methanesulfonamido-spiro[(2H)-1-benzopyran-2,4'-piperidine]-4-one [prepared as described in Example 94, Step B] (45.6 mg, 0.1 mmol) in ethanol (2 ml). The mixture was stirred for 16 hours, then poured into aqueous sodium hydrogen carbonate (saturated, 10 ml) and extracted with dichloromethane (3×10 ml). The combined organic fractions were dried (Na2SO4) and evaporated under reduced pressure to give a pale yellow oil. The residue was dissolved in ethyl acetate (2 ml) and ethanolic HCl (6N, 0.5 ml) was added. The mixture was cooled and the precipitate collected and dried in vacuo to give the hydrochloride as a white solid (32 mg, 65%), m.p.=242°-244° C.

Workup

  1. extractionextracted with dichloromethane (3×10 ml)
  2. dry with materialThe combined organic fractions were dried (Na2SO4)
  3. customevaporated under reduced pressure
  4. customto give a pale yellow oil
  5. temperatureThe mixture was cooled
  6. customthe precipitate collected
  7. customdried in vacuo

Sources & evidence

ORD record
ord-1deef3ab54144803bab9edf9dbee3418
Source dataset
uspto-grants-1997_05
Patent number
US05633247

Reaction notes

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