MeOH tetrahydrofuran → HCID 22476606, compound

HRID 2184404Notes

Reaction equation

HRID 2184404 reaction equation
[OH:1][C:2]1([C:14]2[CH:23]=[CH:22][C:17]([O:18][CH2:19][C:20]#[N:21])=[CH:16][CH:15]=2)[CH2:6][CH2:5][CH2:4][CH:3]1[NH:7][S:8]([CH:11]([CH3:13])[CH3:12])(=[O:10])=[O:9].C1COCC1.CO>C1COCC1>[NH2:21][CH2:20][CH2:19][O:18][C:17]1[CH:22]=[CH:23][C:14]([C:2]2([OH:1])[CH2:6][CH2:5][CH2:4][CH:3]2[NH:7][S:8]([CH:11]([CH3:12])[CH3:13])(=[O:10])=[O:9])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 21899815MeOH tetrahydrofuranHCID 22476595HCID 22476595, compound

Product 1

HCID 22476606HCID 22476606, compoundYield 27.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a 50 mL 3 neck flask with stirrer, borane-THF complex (2 mL, 1M solution) was added syringe wise to 2-[4-(1-hydroxy-2-{[(methylethyl)sulfonyl]amino}cyclopentyl)phenoxy]ethanenitrile (125 mg, 0.37 mmol) in THF (10 mL) while stirring at room temperature under a nitrogen atmosphere. The reaction mixture was then stirred overnight. 3 mL of 1:1 THF/Methanol solution was then added by syringe with severe foaming. After the foaming subsided, the solution was concentrated under reduced vacuum to yield 85 mg as an oil. This material was purified via silica gel chromatography employing the Chromatotron® and using a 2000 micron rotor while eluting with a solvent of methylene chloride/ethyl acetate 9:1 to yield the intermediate title compound (35 mg) as an oil. Ion spray M.S. 341.4 (M*−1).

Workup

  1. stirringThe reaction mixture was then stirred overnight
  2. concentrationthe solution was concentrated under reduced vacuum
  3. customto yield 85 mg as an oil
  4. customThis material was purified via silica gel chromatography
  5. washwhile eluting with a solvent of methylene chloride/ethyl acetate 9:1

Sources & evidence

ORD record
ord-02d25176f734424990c14116d45b3019
Source dataset
uspto-grants-2005_05
Patent number
US06900353B2

Reaction notes

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