[(Methylethyl)sulfonyl][2-(phenylmethoxy)cyclopentyl]amine → (2-Hydroxycyclopentyl)[(methylethyl)sulfonyl]amine

HRID 2184397Notes

Reaction equation

HRID 2184397 reaction equation
[CH3:1][CH:2]([S:4]([NH:7][CH:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[O:13]CC1C=CC=CC=1)(=[O:6])=[O:5])[CH3:3]>[Pd].C(O)C>[OH:13][CH:9]1[CH2:10][CH2:11][CH2:12][CH:8]1[NH:7][S:4]([CH:2]([CH3:3])[CH3:1])(=[O:6])=[O:5]

Participants

4

Reactant 1

HCID 22476580[(Methylethyl)sulfonyl][2-(phenylmethoxy)cyclopentyl]amine

Product 1

HCID 22476566(2-Hydroxycyclopentyl)[(methylethyl)sulfonyl]amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Scheme IA, step B: [(Methylethyl)sulfonyl][2-(phenylmethoxy)cyclopentyl]amine (2.00 g, 6.72 mmol), palladium on carbon (250 mg) and ethanol (50 mL) were combined and placed on the power shaker under a hydrogen atmosphere at 60 psi's overnight. In the morning, the solution was filtered over a Celite® mat and the resulting filtrate was concentrated under reduced vacuum to yield 1.50 g as a viscous oil. TLC showed material was very pure and was used without further purification. Yield=Quantitative. Ion spray M.S. 206 (M*−1). Analysis calculated for C8H17NO3S: Theory: C, 46.35; H, 8.26; N, 6.75. Found: C, 46.27; H, 7.97; N, 6.70.

Workup

  1. customs overnight
  2. filtrationIn the morning, the solution was filtered over a Celite® mat
  3. concentrationthe resulting filtrate was concentrated under reduced vacuum
  4. customto yield 1.50 g as a viscous oil
  5. customwas used without further purification
  6. customYield=Quantitative

Sources & evidence

ORD record
ord-3bcb05a38dad4ee7a60e88a1e369d169
Source dataset
uspto-grants-2005_05
Patent number
US06900353B2

Reaction notes

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