Dicyclohexylcarbodiimide → 3-Phenyl-1-propyl 1-(1,2-dioxo-3,3-dimethylpentyl)-2-piperidinecarboxylate

HRID 1828060Notes

Reaction equation

HRID 1828060 reaction equation
[O:1]=[C:2]([N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[C:16]([OH:18])=[O:17])[C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH2:5][CH3:6].[C:19]1([CH2:25][CH2:26][CH2:27]O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1(N=C=NC2CCCCC2)CCCCC1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>C(Cl)Cl>[O:1]=[C:2]([N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[C:16]([O:18][CH2:27][CH2:26][CH2:25][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:17])[C:3](=[O:9])[C:4]([CH3:7])([CH3:8])[CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 31234BenzenepropanolHCID 220647601-(3,3-Dimethyl-2-oxopentanoyl)piperidine-2-carboxylic acid

Product 1

HCID 98858753-Phenyl-1-propyl 1-(1,2-dioxo-3,3-dimethylpentyl)-2-piperidinecarboxylateYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(1,2-dioxo-3,3-dimethylpentyl)-2-piperidinecarboxylic acid (590 mg; 2.31 mmol), 3-phenylpropanol (520 mg; 3.71 mmol), dicyclohexylcarbodiimide (815 mg; 3.95 mmol), camphorsulphonic acid (180 mg; 0.77 mmol) and 4-dimethyl aminopyridine (95 mg; 0.77 mmol) in methylene chloride (15 mL) was stirred overnight under a nitrogen atmosphere. The reaction mixture was filtered through Celite to remove solids and concentrated in vacuo. The crude material was triturated with several portions of ether, and the ether portions were filtered through Celite to remove solids and concentrated in vacuo. The concentrated filtrate was purified on a flash column (20% ethyl acetate in hexane) to obtain 800 mg (93%) of the product as an oil, 1H NMR (CDCl3, 300 MHz): δ 0.85 (t, 3H); 1.23,1.26 (s, 3H each); 1.63–1.94 (m, 9H); 2.32 (m, 1H); 2.69 (m, 2H); 3.21 (m, 1H); 3.35 (m, 1H); 4.17 (m, 2H); 5.24 (m, 1H); 7.14 (m, 3H); 7.7.23 (m, 2H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customto remove solids
  3. concentrationconcentrated in vacuo
  4. customThe crude material was triturated with several portions of ether
  5. filtrationthe ether portions were filtered through Celite
  6. customto remove solids
  7. concentrationconcentrated in vacuo
  8. customThe concentrated filtrate was purified on a flash column (20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-046f827d184945abb4aced2598018d71
Source dataset
uspto-grants-2006_06
Patent number
US07056935B2

Reaction notes

Loading…