Methanol → N-(4-{1-Ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-2-methyl-phenyl)-N-methyl-methanesulfonamide

HRID 2354256Notes

Reaction equation

HRID 2354256 reaction equation
[CH3:1][C:2]([CH3:33])([CH3:32])[C:3](=[O:31])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:17]2[CH:22]=[CH:21][C:20]([N:23]([CH3:28])[S:24]([CH3:27])(=[O:26])=[O:25])=[C:19]([CH3:29])[CH:18]=2)([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:8][C:7]=1[CH3:30].CO.[BH4-].[Na+]>C1COCC1>[CH2:13]([C:12]([C:17]1[CH:22]=[CH:21][C:20]([N:23]([CH3:28])[S:24]([CH3:27])(=[O:25])=[O:26])=[C:19]([CH3:29])[CH:18]=1)([C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH:3]([OH:31])[C:2]([CH3:32])([CH3:33])[CH3:1])=[C:7]([CH3:30])[CH:8]=1)[CH2:15][CH3:16])[CH3:14]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 11155721N-(4-{1-[4-(3,3-Dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-2-methyl-phenyl)-N-methyl-methanesulfonamide

Product 1

HCID 11477062N-(4-{1-Ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-2-methyl-phenyl)-N-methyl-methanesulfonamideYield 60.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. mixture of N-(4-{1-[4-(3,3-dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-2-methyl-phenyl)-N-methyl-methanesulfonamide (100 mg, 0.21 mmol), MeOH (5 mL), and THF (10 mL) is added NaBH4 (12 mg, 0.32 mmol). The reaction is warmed to RT and stirred for 5 h and concentrated. The residue is partitioned between EtOAc and 0.2 N HCl. The organic phase is Na2SO4 dried, concentrated, and chromatographed (0% to 25% EtOAc/Hex) to give the title compound (60 mg, 60%).

Workup

  1. concentrationconcentrated
  2. customThe residue is partitioned between EtOAc and 0.2 N HCl
  3. customdried
  4. concentrationconcentrated
  5. customchromatographed (0% to 25% EtOAc/Hex)

Sources & evidence

ORD record
ord-7ecc3cabfd684b07aca250fdd67bcdd7
Source dataset
uspto-grants-2010_07
Patent number
US07750184B2

Reaction notes

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