Dichloromethane → HCID 86650568, compound

HRID 1911824Notes

Reaction equation

HRID 1911824 reaction equation
C([C@@H:3]1[C@@H:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:6][C:5]([CH3:15])([CH3:14])[N:4]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=O.C1(P(=[CH:42][CH:43]=[O:44])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl[CH2:46]Cl>>[CH3:14][C:5]1([CH3:15])[N:4]([C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[C@H:3](/[CH:46]=[CH:42]/[CH:43]=[O:44])[C@@H:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:6]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 75051(Triphenylphosphoranylidene)acetaldehydeHCID 9972368HCID 9972368, compound

Product 1

HCID 86650568HCID 86650568, compoundYield 68%

Procedure

Compound tert-butyl (4S,5R)-4-formyl-2,2-dimethyl-5-phenyl-1,3-oxazolidine-3-carboxylate (1.30 g, 4.26 mmol) in dichloromethane (10 ml) at ambient temperature was added to (triphenylphosphoranylidene)acetaldehyde (1.69 g, 5.54 mmol). The reaction mixture was stirred at ambient temperature for 40 h. After removal of the solvent, the residue was purified by using a Biotage Horizon® system (0-20% ethyl acetate/hexanes mixture) to afford the title compound (0.96 g, 68%) as a viscous oil. 1H NMR (CDCl3, 500 MHz): δ9.61 (d, J=7.6 Hz, 1H), 7.42-7.37 (m, 5H), 6.73 (m, 1H), 5.96 (dd, J=15.8, 7.7 Hz, 1H), 4.78 (m, 1H), 4.29 (br, 1H), 1.80-1.41 (m, 15H). LC-MS 354.3 (M+23).

Workup

  1. customAfter removal of the solvent
  2. customthe residue was purified

Sources & evidence

ORD record
ord-fb388348cb5d4c38b215635a8e16c733
Source dataset
uspto-grants-2013_12
Patent number
US08604038B2

Reaction notes

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