HCID 89590802, compound → 1-(1-Hydroxy-1-methylethyl)cyclopropanesulfonamide

HRID 522356Notes

Reaction equation

HRID 522356 reaction equation
[OH:1][C:2]([C:5]1([S:8]([NH:11]C(=O)OCC2C=CC=CC=2)(=[O:10])=[O:9])[CH2:7][CH2:6]1)([CH3:4])[CH3:3]>CO.[Pd]>[OH:1][C:2]([C:5]1([S:8]([NH2:11])(=[O:9])=[O:10])[CH2:6][CH2:7]1)([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 89590802HCID 89590802, compound

Product 1

HCID 692665221-(1-Hydroxy-1-methylethyl)cyclopropanesulfonamideYield 68.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of the product of Step 2 (995 mg) in methanol (30 mL) under nitrogen was added Pd/C (169 mg). The flask was purged with hydrogen and stirred for 3 hours. Celite was added to the reaction mixture and it was filtered through a pad of Celite. The solvent was removed in vacuo. The resulting residue was purified by flash chromatography (ISCO, 0 to 10% methanol in dichloromethane) to afford the desired product (391 mg). 1H NMR (400 MHz, CDCl3): δ (ppm) 4.88 (br s, 2H), 2.58 (s, 1H), 1.44-1.41 (m, 2H), 1.41 (s, 6H), 1.06-1.03 (m, 2H).

Workup

  1. customThe flask was purged with hydrogen
  2. additionCelite was added to the reaction mixture and it
  3. filtrationwas filtered through a pad of Celite
  4. customThe solvent was removed in vacuo
  5. customThe resulting residue was purified by flash chromatography (ISCO, 0 to 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-fd70bef1fd0442bcbe0f70d16edc8730
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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