Dicyclohexylcarbodiimide → N-(2-diethylaminoethyl)-N-(ethyl)-((1R,3R,4S)-1-methyl-4-isopropylcyclohex-3-yloxy)acetamide

HRID 248844

Reaction equation

HRID 248844 reaction equation
[CH3:1][C@@H:2]1[CH2:7][CH2:6][C@@H:5]([CH:8]([CH3:10])[CH3:9])[C@H:4]([O:11][CH2:12][C:13]([OH:15])=O)[CH2:3]1.[CH2:16]([N:18]([CH2:24][CH3:25])[CH2:19][CH2:20][NH:21][CH2:22][CH3:23])[CH3:17].C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[CH2:16]([N:18]([CH2:24][CH3:25])[CH2:19][CH2:20][N:21]([CH2:22][CH3:23])[C:13](=[O:15])[CH2:12][O:11][C@H:4]1[C@H:5]([CH:8]([CH3:9])[CH3:10])[CH2:6][CH2:7][C@@H:2]([CH3:1])[CH2:3]1)[CH3:17]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 66040TriethylethylenediamineHCID 70188612-[[(1R,2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]acetic acid

Product 1

HCID 57193064N-(2-diethylaminoethyl)-N-(ethyl)-((1R,3R,4S)-1-methyl-4-isopropylcyclohex-3-yloxy)acetamideYield 60.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5.0 g of ((1R,3R,4S)-1-methyl-4-isopropylcyclohex-3-yloxy)acetic acid were dissolved in 100 ml of tetrahydrofuran. 3.4 g (=4.2 ml) of N,N,N'-triethylethylenediamine and 5.3 g of dicyclohexylcarbodiimide were added to the solution, and the reaction mixture was stirred at room temperature for 24 hours. The mixture was worked up by concentrating it under reduced pressure. The remaining residue was purified by chromatography on silica gel using dichloromethane/methanol as the eluent. 4.8 g of N-(2- diethylaminoethyl)-N-(ethyl)-((1R,3R,4S)-1-methyl-4-isopropylcyclohex-3-yloxy)acetamide were obtained.

Workup

  1. concentrationby concentrating it under reduced pressure
  2. customThe remaining residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-5a73f691c0374498be7d2285e48061d9
Source dataset
uspto-grants-1993_05
Patent number
US05212173

Linked notes

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