Dichloromethane → HCID 86650568, compound

HRID 1804571Notes

Reaction equation

HRID 1804571 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-08a11baa9f854fdab82a455e4de802c4
Source dataset
uspto-grants-2013_01
Patent number
US08354403B2

Reaction notes

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