1-Propanesulfonyl chloride → [(Methylethyl)sulfonyl][2-(phenylmethoxy)cyclopentyl]amine

HRID 2184396Notes

Reaction equation

HRID 2184396 reaction equation
[CH2:1]([S:4](Cl)(=[O:6])=[O:5])[CH2:2]C.[CH2:8]([O:15][C@H:16]1[CH2:20][CH2:19][CH2:18][C@@H:17]1[NH2:21])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH2:22]1CCN2C(=NCCC2)CC1>C(Cl)Cl>[CH3:22][CH:1]([S:4]([NH:21][CH:17]1[CH2:18][CH2:19][CH2:20][CH:16]1[O:15][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:5])=[O:6])[CH3:2]

Participants

5

Reactant 3

HCID 662791-Propanesulfonyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11908836(1S,2S)-1-Amino-2-benzyloxycyclopentane

Product 1

HCID 22476580[(Methylethyl)sulfonyl][2-(phenylmethoxy)cyclopentyl]amineYield 269%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Scheme IA, step A: In a 250 mL 3 neck flask fitted with a stirrer and thermometer, propanesulfonyl chloride (4.47 g, 1.2 eq) was added dropwise to (1S,2S)-2-benzyloxycyclopentylamine (5.00 g, 10 mmol) and DBU (5.98 g, 1.5 eq) in CH2Cl2 (100 mL) while stirring at 0° C. under a nitrogen atmosphere. The reaction was allowed to warm to room temperature and stirred overnight at this temperature. In the morning, the reaction was diluted with CH2Cl2 (100 mL) and the organic layer was washed two times with H2O, dried over Na2SO4, filtered, and concentrated under reduced vacuum to yield 10.13 g as a viscous oil. This material was purified via silica gel chromatography employing the Water's Prep. 2000 and eluting with a solvent of hexane/ethyl acetate 4:1 to yield the intermediate title compound (8.0 g, 95%) as a white solid. Ion spray M.S. 296 (M*−1). Analysis calculated for C15H23NO3S: Theory: C, 60.58; H, 7.80; N, 4.71. Found: C, 60.39; H, 7.79; N, 4.73.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred overnight at this temperature
  3. washthe organic layer was washed two times with H2O
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced vacuum
  7. customto yield 10.13 g as a viscous oil
  8. customThis material was purified via silica gel chromatography
  9. wash2000 and eluting with a solvent of hexane/ethyl acetate 4:1

Sources & evidence

ORD record
ord-4add604acaa54ed0b04a8fa6c548f0c0
Source dataset
uspto-grants-2005_05
Patent number
US06900353B2

Reaction notes

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