3,3,5-Trimethylcyclohexanol → HCID 22845142, compound

HRID 654835Notes

Reaction equation

HRID 654835 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C:15](=[O:16])[CH2:14][CH2:13][C@H:12]1[C:17]([OH:19])=[O:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C1C=CC=CN=1)C.[CH3:29][C:30]1([CH3:38])[CH2:35][CH:34]([CH3:36])[CH2:33][CH:32](O)[CH2:31]1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[CH2:1]([O:8][C:9]([N:11]1[C:15](=[O:16])[CH2:14][CH2:13][C@H:12]1[C:17]([O:19][CH:32]1[CH2:33][CH:34]([CH3:36])[CH2:35][C:30]([CH3:38])([CH3:29])[CH2:31]1)=[O:18])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 82983,3,5-TrimethylcyclohexanolHCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 6376481-(Phenylmethyl) (2S)-5-oxo-1,2-pyrrolidinedicarboxylate

Product 1

HCID 22845142HCID 22845142, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

34.2 g (0.13 mol) of N-benzyloxycarbonyl-L-pyroglutamic acid (prepared according to Berichte 97, 2434 [1964] or Annalen 649, 183 [1961] ) are added to 150 ml of dimethylformamide, followed by 2 g of dimethylaminopyridine and then 18.48 g (0.13 mol) of 3,3,5-trimethylcyclohexanol (mixture of 90% trans isomer and 10% cis isomer) diluted in 50 ml of dimethylformamide. 26.8 g (0.13 mol) of dicyclohexylcarbodiimide are then run in over a period of about 15 minutes, the reaction medium being kept at +5° C. The mixture is then stirred at room temperature for 24 hours, after which the solvent is evaporated off, the residue is taken up with dilute hydrochloric acid and extraction is carried out with chloroform.

Workup

  1. customare then run in over a period of about 15 minutes
  2. custombeing kept at +5° C
  3. customafter which the solvent is evaporated off
  4. extractionthe residue is taken up with dilute hydrochloric acid and extraction

Sources & evidence

ORD record
ord-66651c66750d4be383bc594105b77fa0
Source dataset
uspto-grants-1992_07
Patent number
US05134157

Reaction notes

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