(1R)-2-{[6-({4-[4-(cyclopentylsulfonyl)phenyl]but-3-ynyl}oxy)hexyl]amino}-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol → (1R)-2-[(6-{4-[4-(Cyclopentylsulfonyl)phenyl]butoxy}hexyl)amino]-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol

HRID 2118331Notes

Reaction equation

HRID 2118331 reaction equation
[CH:1]1([S:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]#[C:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][CH2:27][C@@H:28]([C:30]3[CH:41]=[CH:40][C:33]4[O:34][C:35]([CH3:39])([CH3:38])[O:36][CH2:37][C:32]=4[CH:31]=3)[OH:29])=[CH:11][CH:10]=2)(=[O:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1>CCOC(C)=O.[Pd]>[CH:1]1([S:6]([C:9]2[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][CH2:27][C@@H:28]([C:30]3[CH:41]=[CH:40][C:33]4[O:34][C:35]([CH3:38])([CH3:39])[O:36][CH2:37][C:32]=4[CH:31]=3)[OH:29])=[CH:13][CH:14]=2)(=[O:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 69119804(1R)-2-{[6-({4-[4-(cyclopentylsulfonyl)phenyl]but-3-ynyl}oxy)hexyl]amino}-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol

Product 1

HCID 69119881(1R)-2-[(6-{4-[4-(Cyclopentylsulfonyl)phenyl]butoxy}hexyl)amino]-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanolYield 50.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (1R)-2-{[6-({4-[4-(cyclopentylsulfonyl)phenyl]but-3-ynyl}oxy)hexyl]amino}-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol (127 mg) in EtOAc (10 ml) was hydrogenated over a palladium on carbon catalyst (50% water by weight, 6.35 mg) for 19 h. The catalyst was removed by filtration and the filtrate was evaporated to dryness. The residual oil was purified on a silica bond elut SPE cartridge (5 g), gradient 0% to 20% [MeOH-aqueous ammonia(10:1)] in DCM (Gradmaster™). The appropriate fractions were evaporated to give the title compound (65 mg) LCMS RT=2.85 min

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated to dryness
  3. customThe residual oil was purified on a silica bond
  4. customThe appropriate fractions were evaporated

Sources & evidence

ORD record
ord-e6fb58dd9f63446cb7ef0218b1290fe1
Source dataset
uspto-grants-2008_10
Patent number
US07442839B2

Reaction notes

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