Cyclohexanecarboxylic acid, 2-(2-(benzylcarbamoyl)ethyl)hydrazide → rac-(2R,5S)-1-benzylpyrrolidine-2,5-dicarboxylic acid

HRID 1605942Notes

Reaction equation

HRID 1605942 reaction equation
[CH2:1]([N:8]1[C@H:12]([C:13]([O:15]CC)=[O:14])[CH2:11][CH2:10][C@@H:9]1[C:18]([O:20]CC)=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1CCC(C(NNCCC(NCC2C=CC=CC=2)=O)=O)CC1>Cl>[CH2:1]([N:8]1[C@H:9]([C:18]([OH:20])=[O:19])[CH2:10][CH2:11][C@@H:12]1[C:13]([OH:15])=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 204154Cyclohexanecarboxylic acid, 2-(2-(benzylcarbamoyl)ethyl)hydrazideHCID 6932547(2S,5R)-Diethyl 1-benzylpyrrolidine-2,5-dicarboxylate2×

Product 1

HCID 26202186rac-(2R,5S)-1-benzylpyrrolidine-2,5-dicarboxylic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The first step in the preparation of this compound was to prepare diethyl cis-N-benzylpyrrolidine-2,5-dicarboxylate from diethyl meso-α,α'-dibromoadipate (see Example 1) as described by G. Cignarella and G. Nathansohn in J. Org. Chem., 26, p 1500, 1961. Diethyl cis-N-benzylpyrrolidine-2,5-dicarboxylate (103.5 g, 0.340 mole) was then heated in 1 liter concentrated hydrochloric acid at 100° C for 2 hours. Upon cooling, a crystalline solid precipitated. It was isolated by filtration, triturated with acetone-diethyl ether, and recrystallized from ethanol-water to give 41.3 g (49%) of partially hydrated product, melting point 254°-258° C. An infrared spectrum analysis gave λmax.Nujol = 2.95 μ (O--H).

Workup

  1. customThe first step in the preparation of this compound
  2. temperatureUpon cooling
  3. customa crystalline solid precipitated
  4. customIt was isolated by filtration
  5. customtriturated with acetone-diethyl ether
  6. customrecrystallized from ethanol-water
  7. customto give 41.3 g (49%) of partially hydrated product, melting point 254°-258° C
  8. customAn infrared spectrum analysis gave λmax.Nujol = 2.95

Sources & evidence

ORD record
ord-4c5004b1a0784ecca32e7006e23676cd
Source dataset
uspto-grants-1976_04
Patent number
US03951980

Reaction notes

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