Triethylamine → (2R,3R)-2-Methyl-3-phenylaziridine

HRID 1661468Notes

Reaction equation

HRID 1661468 reaction equation
[CH3:1][C@H:2]([NH2:11])[C@H:3](O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.C(N(CC)CC)C>C1COCC1.CCCCCC>[CH3:1][C@@H:2]1[C@@H:3]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:11]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10297PhenylpropanolamineHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylate

Product 1

HCID 11263513(2R,3R)-2-Methyl-3-phenylaziridine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To (1R,2S)-(−)-norephedrine (1 g, 6.61 mmol) in THF (20 mL), triphenylphosphine (1.98 ml, 7.94 mmol), diisopropyl azodicarboxylate (1.401 ml, 7.27 mmol) and triethylamine (2.6 ml, 18.8 mmol) was added anr the rm was stirred at room temperature over night. The solvent was evaporated and the crude material was purified on silica eluting with Heptane/EtPAc 1+4 to EtOAc 100% and EtOAc/MeOH 95+5% the fractions containing product were collected giving 2.5 g of with solid containing lot of P(Ph)3O according to LC/MS. This solid was stirred in hexane (50 ml) O/N and than filtered through a pad of Celite 545 giving 0.6 g of an oil.

Workup

  1. customThe solvent was evaporated
  2. customthe crude material was purified on silica eluting with Heptane/EtPAc 1+4 to EtOAc 100% and EtOAc/MeOH 95+5% the fractions
  3. additioncontaining product
  4. customwere collected
  5. customgiving 2.5 g of with solid
  6. filtrationthan filtered through a pad of Celite 545 giving 0.6 g of an oil

Sources & evidence

ORD record
ord-03040d309f8340bea089be2cd7ca432e
Source dataset
uspto-grants-2011_10
Patent number
US08030340B2

Reaction notes

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