Boron trifluoride → HCID 57979844, compound

HRID 1867733Notes

Reaction equation

HRID 1867733 reaction equation
B(F)(F)F.[N:5]1([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH2:7][C@H:6]1[C:8]([O:10][CH3:11])=[O:9].[CH:22]([OH:25])([CH3:24])[CH3:23].ClCCl>ClCCl>[CH2:15]([O:14][C:12]([NH:5][C@H:6]([C:8]([O:10][CH3:11])=[O:9])[CH2:7][O:25][CH:22]([CH3:24])[CH3:23])=[O:13])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 6356Boron trifluorideHCID 6434641-Benzyl 2-methyl aziridine-1,2-dicarboxylateHCID 21966342Isopropanol methylene chloride

Product 1

HCID 57979844HCID 57979844, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

16 syringe drops of boron trifluoride diethyletherate (catalyst) was added to a stirred solution of 1-benzyl 2-methyl (2S)-aziridine-1,2-dicarboxylate (0.50 g, 2.1 mmol) in isopropanol/dichloromethane (30 ml, 1:2) at room temperature. The resulting solution was stirred overnight at room temperature. The reaction mixture was diluted with dichloromethane (20 ml), washed with a saturated aqueous sodium bicarbonate (5 ml), water (5 ml), dried over magnesium sulfate, filtered and concentrated to give methyl N-[(benzyloxy)carbonyl]-O-isopropyl-L-serinate as a clear colourless oil, (0.432 g, 68%); 1H NMR Spectrum: (CDCl3) 1.09 (m, 6H), 3.56 (m, 1H), 3.65 (m, 1H), 3.79 (s, 3H), 3.82 (m, 1H), 4.46 (m, 1H), 5.16 (s, 2H), 5.60 (d, 1H), 7.38 (m, 5H).

Workup

  1. washwashed with a saturated aqueous sodium bicarbonate (5 ml), water (5 ml)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-193356df45b0433181c16b44a9fcc66f
Source dataset
uspto-grants-2009_12
Patent number
US07632840B2

Reaction notes

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