Hydroxylamine → HCID 87599065, compound

HRID 1723822Notes

Reaction equation

HRID 1723822 reaction equation
[F:1][C:2]([F:30])([O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][N:16]([S:19](/[CH:22]=[CH:23]/[CH:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)(=[O:21])=[O:20])[CH2:15][CH2:14]2)=[CH:9][CH:8]=1)[CH:3]([F:5])[F:4].[NH2:31][OH:32]>C1COCC1.O>[OH:32][NH:31][CH:23]([CH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)[CH2:22][S:19]([N:16]1[CH2:17][CH2:18][N:13]([C:10]2[CH:9]=[CH:8][C:7]([O:6][C:2]([F:1])([F:30])[CH:3]([F:4])[F:5])=[CH:12][CH:11]=2)[CH2:14][CH2:15]1)(=[O:20])=[O:21]

Participants

5

Reactant 2

HCID 787HydroxylamineHCID 86614579HCID 86614579, compound

Product 1

HCID 87599065HCID 87599065, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-4-{[(E)-2-(tetrahydro-2H-pyran-4-yl)vinyl]sulfonyl}piperazine (3.13 g, 0.007 mol) was dissolved in THF (50 ml) and 50% hydroxylamine in H2O (12 ml) was added. Stirred at ambient temperature overnight, quenched with saturated NH4Cl solution and extracted with ethyl acetate. The organic phase was dried over MgSO4, filtered and evaporated to dryness to yield racemic 1-{[2-(hydroxyamino)-2-(tetrahydro-2H-pyran-4-yl)ethyl]sulfonyl}-4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]piperazine This was separated into its enantiomers using an AD Chiralpak chiral prep HPLC column and eluting with 20% methanol/acetonitrile. The second compound off the column gave the required enantiomer, 1-{[(2S)-2-(hydroxyamino)-2-(tetrahydro-2H-pyran-4-yl)ethyl]sulfonyl}-4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]piperazine.

Workup

  1. customquenched with saturated NH4Cl solution
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-eea6f5efc4074cc09887a255b3141c6c
Source dataset
uspto-grants-2009_02
Patent number
US07485644B2

Reaction notes

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