Boron trifluoride etherate → (alphaR,betaR)-N-benzyloxycarbonyl-1,beta-dimethyltryptophane methyl ester

HRID 1382241Notes

Reaction equation

HRID 1382241 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3]1.[CH2:11]([O:18][C:19]([N:21]1[C@H:23]([CH3:24])[C@@H:22]1[C:25]([O:27][CH3:28])=[O:26])=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.B(F)(F)F.CCOCC>C(Cl)Cl>[CH3:28][O:27][C:25](=[O:26])[C@@H:22]([C@H:23]([CH3:24])[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:2]([CH3:1])[CH:3]=1)[NH:21][C:19]([O:18][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:20]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 117811-MethylindoleHCID 11161001methyl (2R,3R)-N-benzyloxycarbonyl-3-methyl-2-aziridinecarboxylate

Product 1

HCID 22841449(alphaR,betaR)-N-benzyloxycarbonyl-1,beta-dimethyltryptophane methyl esterYield 39.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1-methylindole (4.26 g) and methyl (2R,3R)-N-benzyloxycarbonyl-3-methyl-2-aziridinecarboxylate (2.70 g) in dry methylene chloride (50 ml) was added boron trifluoride etherate (1.33 ml) under ice-bath cooling. The mixture was stirred for five minutes at ambient temperature and the solvent was evaporated off. The residue was chromatographed on silica gel (chloroform and a 1:1 mixture of hexane and ether as eluent) to give (αR,βR)-N-benzyloxycarbonyl-1,β-dimethyltryptophane methyl ester (1.62 g) as an oil.

Workup

  1. temperaturecooling
  2. customthe solvent was evaporated off
  3. customThe residue was chromatographed on silica gel (chloroform
  4. additiona 1:1 mixture of hexane and ether as eluent)

Sources & evidence

ORD record
ord-ffe94c07938f4e25861b25cdab09a082
Source dataset
uspto-grants-1989_02
Patent number
US04806538

Reaction notes

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