(2-Hydroxycyclopentyl)[(methylethyl)sulfonyl]amine → HCID 22476614, compound

HRID 2184398Notes

Reaction equation

HRID 2184398 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[NH:7][S:8]([CH:11]([CH3:13])[CH3:12])(=[O:10])=[O:9].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH3:13][CH:11]([S:8]([NH:7][CH:3]1[CH2:4][CH2:5][CH2:6][C:2]1=[O:1])(=[O:10])=[O:9])[CH3:12]

Participants

4

Reactant 2

HCID 22476566(2-Hydroxycyclopentyl)[(methylethyl)sulfonyl]amineHCID 178418287HCID 178418287, compound

Product 1

HCID 22476614HCID 22476614, compoundYield 30.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Scheme IA, step C: Into a 250 mL single neck flask, (2-hydroxycyclopentyl)[(methylethyl)sulfonyl]amine (1.5 g, 7.24 mmol), pyridinium chlorochromate (2.34 g, 1.5 eq) and methylene chloride (100 mL) were mixed together and stirred for 4 hours at room temperature under a nitrogen atmosphere. The solution was then filtered over a Celite® mat and the resulting filtrate was washed once with water, dried over potassium carbonate, and concentrated under reduced vacuum to yield 1.31 g as an oil. This material was purified via silica gel chromatography employing the Chromatotron® and using a 4000 micron rotor while eluting with a solvent of methylene chloride/ethyl acetate 4:1 to yield the intermediate title compound (450 mg, 30%) as a slowly crystallizing oil. Ion spray M.S. 204 (M*−1). Analysis calculated for C8H15NO3S: Theory: C, 46.81; H, 7.37; N, 6.82. Found: C, 46.08; H, 7.12; N, 6.58.

Workup

  1. filtrationThe solution was then filtered over a Celite® mat
  2. washthe resulting filtrate was washed once with water
  3. dry with materialdried over potassium carbonate
  4. concentrationconcentrated under reduced vacuum
  5. customto yield 1.31 g as an oil
  6. customThis material was purified via silica gel chromatography
  7. washwhile eluting with a solvent of methylene chloride/ethyl acetate 4:1

Sources & evidence

ORD record
ord-5e1b64aa66b94335b425889a0e79a250
Source dataset
uspto-grants-2005_05
Patent number
US06900353B2

Reaction notes

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