2-[(Benzyloxy)methyl]-1-tritylaziridine → 2-[(Benzyloxy)methyl]aziridine

HRID 2109844Notes

Reaction equation

HRID 2109844 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]1[CH2:12][N:11]1C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>ClCCl.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>[CH2:1]([O:8][CH2:9][CH:10]1[CH2:12][NH:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 781562322-[(Benzyloxy)methyl]-1-tritylaziridine

Product 1

HCID 866027862-[(Benzyloxy)methyl]aziridine

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolventHCID 12052TriethylsilaneSolvent

Procedure

To a cold (0° C.) solution of 2-[(benzyloxy)methyl]-1-tritylaziridine (1.28 g, 3.16 mmol) in dichloromethane (13 mL), trifluoroacetic acid (1 mL) and triethylsilane (2.0 mL) was added and stirred at the temperature for 1 h. The resultant mixture was concentrated under vacuum, and the residue was partitioned between ether and brine. The organic extract was dried with anhydrous magnesium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with a mixture of 50-100% THF in hexane. Collection and concentration of appropriate fractions provided 2-[(benzyloxy)methyl]aziridine.

Workup

  1. concentrationThe resultant mixture was concentrated under vacuum
  2. customthe residue was partitioned between ether and brine
  3. extractionThe organic extract
  4. dry with materialwas dried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. additionThe residue was subjected to column chromatography on silica gel eluting with a mixture of 50-100% THF in hexane
  8. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-22c1b535cf6d413b91a75cd5230e7cd9
Source dataset
uspto-grants-2009_04
Patent number
US07517532B2

Reaction notes

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