Water → HCID 22476617, compound

HRID 2184414Notes

Reaction equation

HRID 2184414 reaction equation
[OH:1][C:2]1([C:15]2[CH:24]=[CH:23][C:18]([O:19][CH2:20][C:21]#[N:22])=[CH:17][CH:16]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[NH:8][S:9]([CH:12]([CH3:14])[CH3:13])(=[O:11])=[O:10].COCCO[AlH2-]OCCOC.[Na+].O>C1COCC1.C1(C)C=CC=CC=1.C1(C)C=CC=CC=1>[NH2:22][CH2:21][CH2:20][O:19][C:18]1[CH:23]=[CH:24][C:15]([C:2]2([OH:1])[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]2[NH:8][S:9]([CH:12]([CH3:13])[CH3:14])(=[O:11])=[O:10])=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 962WaterHCID 16684438Red-AlHCID 22476609HCID 22476609, compound

Product 1

HCID 22476617HCID 22476617, compoundYield 118.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 22635083Tetrahydrofuran tolueneSolvent

Procedure

Into a 100 mL, 3 neck flask with stirrer, 2-[4-(1-hydroxy-2-{[(methylethyl)sulfonyl]amino}cyclohexyl)phenoxy]ethanenitrile (400 mg) in THF-toluene 1:1 (30 mL) was added dropwise to Red-Al® (3 mL, 65% solution in toluene) while stirring at room temperature under a nitrogen atmosphere. The reaction mixture was then stirred for two hours at this temperature. The mixture was poured into water and the desired material was extracted with ethyl acetate. The organic layer was washed once with water, dried over potassium carbonate, filtered, and concentrated under reduced vacuum to yield the intermediate title compound (478 mg, 89%) as a white foam. This material was used without further purification. Ion spray M.S. 355.2 (M*−1). Calculated for C17H28N2O4S-H2O: Theory: C 54.51, H 8.07. Found: C 54.20, H 8.29.

Workup

  1. stirringThe reaction mixture was then stirred for two hours at this temperature
  2. extractionthe desired material was extracted with ethyl acetate
  3. washThe organic layer was washed once with water
  4. dry with materialdried over potassium carbonate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced vacuum

Sources & evidence

ORD record
ord-455acb8b473d4f7f9c93ef365945288f
Source dataset
uspto-grants-2005_05
Patent number
US06900353B2

Reaction notes

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