Methanol → HCID 86614578, compound

HRID 1723820Notes

Reaction equation

HRID 1723820 reaction equation
[F:1][C:2]([F:31])([O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][N:16]([S:19]([CH2:22][C:23]([CH:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[O:24])(=[O:21])=[O:20])[CH2:15][CH2:14]2)=[CH:9][CH:8]=1)[CH:3]([F:5])[F:4].CO.[BH4-].[Na+].O>C(Cl)Cl>[F:31][C:2]([F:1])([O:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]2[CH2:18][CH2:17][N:16]([S:19]([CH2:22][CH:23]([CH:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[OH:24])(=[O:21])=[O:20])[CH2:15][CH2:14]2)=[CH:11][CH:12]=1)[CH:3]([F:4])[F:5]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 86614577HCID 86614577, compound

Product 1

HCID 86614578HCID 86614578, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Crude 2-({4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]piperazin-1-yl}sulfonyl)-1-(tetrahydro-2H-pyran-4-yl)ethanone (3.60 g, 0.008M) was dissolved in DCM (120 ml) and methanol (40 ml) at ambient temperature and sodium borohydride (334 mg, 0.0088 mol) was added. Stirred for 2 hours, added H2O (250 ml) and extracted with DCM. Collected the organic phase, dried over MgSO4, filtered and evaporated to dryness to yield 2-({4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]piperazin-1-yl}sulfonyl)-1-(tetrahydro-2H-pyran-4-yl)ethanol (3.6 g, 95%).

Workup

  1. extractionextracted with DCM
  2. customCollected the organic phase
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-5bfa041710d945728aee9dbed3876711
Source dataset
uspto-grants-2009_02
Patent number
US07485644B2

Reaction notes

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