Nitrogen → (R)-2-(1-Benzyl-cyclopropylmethyl)-succinic acid 1-methyl ester

HRID 1796135Notes

Reaction equation

HRID 1796135 reaction equation
[CH3:1][O:2][C:3](=[O:20])/[C:4](=[CH:9]\[C:10]1([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:12][CH2:11]1)/[CH2:5][C:6]([OH:8])=[O:7].C[O-].[Na+].N#N>CO>[CH3:1][O:2][C:3](=[O:20])[C@H:4]([CH2:9][C:10]1([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:11][CH2:12]1)[CH2:5][C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 947NitrogenHCID 10942334Sodium MethoxideHCID 696193682-[1-(1-Benzyl-cyclopropyl)-meth-(Z)-ylidene]-succinic acid 1-methyl ester

Product 1

HCID 69619387(R)-2-(1-Benzyl-cyclopropylmethyl)-succinic acid 1-methyl esterYield 91.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-[1-(1-Benzyl-cyclopropyl)-meth-(Z)-ylidene]-succinic acid 1-methyl ester (2.686 g, 9.79 mmol) and sodium methoxide (0.1 eq., 0.98 mmol, 52.9 mg) in dry methanol (25 mL) was degassed with N2 for 5 min then (+)-(2S,5S)-2,5-Diethylphospholanobenzene (cyclooctadiene) Rhodium tetrafluoroborate (25 mg) was added. The mixture was hydrogenated at 60 psi for 24 hr, then concentrated in vacuum. The residue was diluted with NaHCO3 (150 mL) and the solution was made basic with NaOH and extracted with ether (80 mL). The aqueous layer was acidified to pH 1 and extracted with ether (2×100 mL). The acidic extracts were dried (MgSO4) and concentrated in vacuum to afford (R)-2-(1-Benzyl-cyclopropylmethyl)-succinic acid 1-methyl ester as a yellow oil (2.465 g, 91% yield).

Workup

  1. concentrationconcentrated in vacuum
  2. additionThe residue was diluted with NaHCO3 (150 mL)
  3. extractionextracted with ether (80 mL)
  4. extractionextracted with ether (2×100 mL)
  5. dry with materialThe acidic extracts were dried (MgSO4)
  6. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-846f0c91b56c441c8225092d441a1b48
Source dataset
uspto-grants-2006_04
Patent number
US07030116B2

Reaction notes

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