Dicyclohexylcarbodiimide → 8-Benzyl-3-oxa-8-azabicyclo[3.2.1]octane-2,4-dione

HRID 1743698Notes

Reaction equation

HRID 1743698 reaction equation
[CH2:1]([N:8]1[C@H:12]([C:13]([OH:15])=O)[CH2:11][CH2:10][C@@H:9]1[C:16]([OH:18])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(N=C=NC2CCCCC2)CCCCC1>C1COCC1>[CH2:1]([N:8]1[CH:9]2[CH2:10][CH2:11][CH:12]1[C:13](=[O:15])[O:18][C:16]2=[O:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 26202186rac-(2R,5S)-1-benzylpyrrolidine-2,5-dicarboxylic acid

Product 1

HCID 222355968-Benzyl-3-oxa-8-azabicyclo[3.2.1]octane-2,4-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of cis-1-benzyl-2,5-pyrrolidinedicarboxylic acid (60 g, 0.24 mol; from Preparation A, step (c) above) and dicyclohexylcarbodiimide (49.7 g, 0.24 mol) in THF (1.2 L) was heated at reflux for 18 hours. The reaction was cooled and filtered to remove the urea by-product. The filtrate was concentrated in vacuo to afford a dark brown viscous oil which was used in the next step without further purification.

Workup

  1. temperatureat reflux for 18 hours
  2. temperatureThe reaction was cooled
  3. filtrationfiltered
  4. customto remove the urea by-product
  5. concentrationThe filtrate was concentrated in vacuo
  6. customto afford a dark brown viscous oil which
  7. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-f7984d0f1a1c48c9b6f1dc53df2c21e7
Source dataset
uspto-grants-2006_03
Patent number
US07012074B2

Reaction notes

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