Hydroxyamine hydrochloride → HCID 11197008, compound

HRID 509189Notes

Reaction equation

HRID 509189 reaction equation
[CH:1]([N:14]1C(C2C=CC(OC)=CC=2)[O:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.NO>CO>[CH:1]([NH:14][OH:15])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 13635628HCID 13635628, compound

Product 1

HCID 11197008HCID 11197008, compoundYield 20.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-benzhydryl-3-(4-methoxyphenyl)-1,2-oxaziridine 40 (3.52 g, 11.1 mmol) in methanol (100 mL) was added hydroxylamine-HCl (2.31 g, 33.3 mmol) and stirred at room temperature. for 16 h. The reaction mixture was concentrated under vacuum and diluted with aqueous NaOH solution (to pH=13), followed by extraction with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated. The crude material was concentrated and purified by silica gel column chromatography with gradient of ethyl acetate (10-50%) in hexane to afford compound 41 as a light yellow solid (450 mg, 20%). LRMS (ESI): (calc.) 199.3 (found) 167.2 (M-NHOH)+.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. additiondiluted with aqueous NaOH solution (to pH=13)
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. concentrationThe crude material was concentrated
  8. custompurified by silica gel column chromatography with gradient of ethyl acetate (10-50%) in hexane

Sources & evidence

ORD record
ord-3745e57776ff473899db7ca4c4c6fd83
Source dataset
uspto-grants-2015_08
Patent number
US09096565B2

Reaction notes

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