Hydrochloric Acid → HCID 86743791, compound

HRID 345361Notes

Reaction equation

HRID 345361 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:10][CH2:9][C@H:8]([CH2:11][CH:12]=O)[C@@H:7]1[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:5])[CH3:2].[Cl-].[CH3:20][O:21]C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].O1CCCC1.Cl>O1CCCC1>[CH2:1]([O:3][C:4]([N:6]1[CH2:10][CH2:9][C@H:8]([CH2:11][CH2:12][CH:20]=[O:21])[C@@H:7]1[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 66863523KOtBu THFHCID 86743790HCID 86743790, compound

Product 1

HCID 86743791HCID 86743791, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 0.663 g of cis 1-ethoxycarbonyl-2-ethoxycarbonyl-pyrrolidine-3-acetaldehyde in 10 ml anhydrous tetrahydrofuran under nitrogen, cooled to -78°, is added dropwise a solution of 2.21 g of methoxymethyl-triphenylphosphonium chloride in 20 ml of anhydrous tetrahydrofuran to which is added 2.6 ml of potassium tert-butoxide/tetrahydrofuran (1.6M). Solution is stirred at room temperature for 4 hours; 15 ml of 2N hydrochloric acid is added and the mixture stirred for 45 minutes. The solution is concentrated and then extracted with methylene chloride. The extract is dried over sodium sulfate, filtered and concentrated; purification by flash chromatography using ethyl acetate/hexane (1:5 to 3:7) yields cis 1-ethoxycarbonyl-2-ethoxycarbonylpyrrolidine-3-propionaldehyde.

Workup

  1. stirringthe mixture stirred for 45 minutes
  2. concentrationThe solution is concentrated
  3. extractionextracted with methylene chloride
  4. dry with materialThe extract is dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurification by flash chromatography

Sources & evidence

ORD record
ord-79c9173d69de4ebe89c7d8068a7fae28
Source dataset
uspto-grants-1991_10
Patent number
US05057506

Reaction notes

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