1-Allyl-1-cyclohexanol → 1-((1-Tosylaziridin-2-yl)methyl)cyclohexanol

HRID 1254317Notes

Reaction equation

HRID 1254317 reaction equation
[CH2:1]([C:4]1([OH:10])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)[CH:2]=[CH2:3].[C:11]1([CH3:33])[CH:16]=[CH:15][C:14]([S:17]([N:20]=C2CCCCI2C2C=CC=CC=2)(=[O:19])=[O:18])=[CH:13][CH:12]=1>C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Cu+2].C(#N)C>[S:17]([N:20]1[CH2:3][CH:2]1[CH2:1][C:4]1([OH:10])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)([C:14]1[CH:15]=[CH:16][C:11]([CH3:33])=[CH:12][CH:13]=1)(=[O:19])=[O:18]

Participants

5

Reactant 2

HCID 791451-Allyl-1-cyclohexanolHCID 86611515N-tosyliminophenyliodinane

Product 1

HCID 593828311-((1-Tosylaziridin-2-yl)methyl)cyclohexanolYield 13.3%

Reagents, catalysts & solvents 2

HCID 2734996copper(II) trifluoromethanesulfonateCatalystHCID 6342AcetonitrileSolvent

Procedure

A flame-dried 100 mL three-necked flask was purged with N2, and charged with Cu(OTf)2 (95 mg, 0.26 mmol), 1-allylcyclohexanol (960 mg, 9.86 mmol) and acetonitrile (HPLC grade). Solid [N-(p-Toluenesulfonyl)imino]phenyliodinane (PhINTs, prepared as described in Inorgania Chimica Acta 2003, 342, 301-304, 1.97 g, 5.28 mmol) was added in a single portion and the mixture was stirred at rt until all PhINTs had dissolved (within 5 to 30 min). The solvent was removed and the residue was chromatographied on silica gel eluted with hexane/EtOAc to give 1-((1-tosylaziridin-2-yl)methyl)cyclohexanol (217 mg, 13%). MS m/z 310 (M+H+).

Workup

  1. customA flame-dried 100 mL three-necked flask was purged with N2
  2. dissolutionhad dissolved (within 5 to 30 min)
  3. customThe solvent was removed
  4. washeluted with hexane/EtOAc

Sources & evidence

ORD record
ord-780333f8af1742eda1ffa10ba324d5d1
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

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