Triethyl phosphonoacetate → HCID 22864771, compound

HRID 1078710Notes

Reaction equation

HRID 1078710 reaction equation
C(OP([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[C:17]([O:21][C:22]([N:24]1[CH2:28][C@H:27]([O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[CH2:26][C@H:25]1[CH2:37][CH:38]=O)=[O:23])([CH3:20])([CH3:19])[CH3:18].S([O-])(O)(=O)=O.[K+]>O1CCCC1>[C:17]([O:21][C:22]([N:24]1[CH2:28][C@H:27]([O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[CH2:26][C@H:25]1[CH2:37]/[CH:38]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:23])([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 516920Potassium bisulfateHCID 10807344HCID 10807344, compound

Product 1

HCID 22864771HCID 22864771, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice-cooled solution of ethyl diethylphosphonoacetate (1.1 ml, 5.54 mmol) in tetrahydrofuran (10 ml) was added sodium hydride (60%, in oil suspension, 220 mg, 5.5 mmol) under a nitrogen atmosphere, and the mixture was stirred for 30 min at the same temperature. To the ice-cooled reaction mixture was added a solution of (2S,4R)-N-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-(formylmethyl)pyrrolidine (1.72 g, 5.01 mmol) in tetrahydrofuran (3 ml), and the mixture was stirred for 1 h. The reaction mixture was poured into a mixture of ice water (200 ml) and 1N aqueous potassium hydrogensulfate (20 ml), and extracted with ethyl acetate (3×50 ml). The combined organic layer was washed successively with water and saturated aqueous sodium chloride, and dried over anhydrous sodium sulfate. The solvent was removed in vacuo, and the residue was subjected to silica gel column chromatography (heptane-ethyl acetate) to give (2R,4R)-N-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-[(E)-3-ethoxycarbonylallyl]pyrrolidine (1.98 mg, yield: 96%).

Workup

  1. customreaction mixture
  2. stirringthe mixture was stirred for 1 h
  3. extractionextracted with ethyl acetate (3×50 ml)
  4. washThe combined organic layer was washed successively with water and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-66f4b8a1b0af426bba5780b1f8a5abfc
Source dataset
uspto-grants-1996_08
Patent number
US05550121

Reaction notes

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