1,8-Diazabicyclo(5.4.0)undec-7-ene → 2,3-diethyl (2R,3R)-oxirane-2,3-dicarboxylate

HRID 1478620Notes

Reaction equation

HRID 1478620 reaction equation
[O:1]1[C@H:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C@H:2]1[C:9]([O:11][CH2:12][CH3:13])=[O:10].Br[C@@H]([C@@H](O)C(OCC)=O)C(OCC)=O.C1CCN2C(=NCCC2)CC1>CCOCC>[O:1]1[C@@H:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C@@H:2]1[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 7021072diethyl (2S,3S)-oxirane-2,3-dicarboxylateHCID 10901630Diethyl (2S,3S)-2-bromo-3-hydroxysuccinate

Product 1

HCID 27336462,3-diethyl (2R,3R)-oxirane-2,3-dicarboxylateYield 74.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Followed general procedure for 3a using the following quantities: 2b (34.6 g, 129 mmol): Et2O (100 ml); DBU (29.4 g, 193 mmol, in Et2O [50 ml]); yielded 3b as a colorless oil (18.1 g, 74.8%). 1H NMR (CDCl3, 400 MHz): δ 4.36-4.22 (m, 4H); 3.67 (s, 2H); 1.35-1.31 (t, 6H). 13C NMR (CDCl3, 100 MHz): 166.75, 62.21, 52.01, 14.01.

Sources & evidence

ORD record
ord-fa2dbd3d26774a96ad5bb6d6135f93f6
Source dataset
uspto-grants-2016_08
Patent number
US09403843B2

Reaction notes

Loading…