1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178502733, compound

HRID 2389193Notes

Reaction equation

HRID 2389193 reaction equation
[OH:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([OH:10])=O)[CH2:4][CH2:3]1.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C.Cl.[CH3:32][NH:33][O:34][CH3:35]>C(Cl)Cl.O>[OH:1][C@@H:2]1[CH2:3][CH2:4][C@H:5]([C:8]([N:33]([O:34][CH3:35])[CH3:32])=[O:10])[CH2:6][CH2:7]1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 178525779HCID 178525779, compound

Product 1

HCID 178502733HCID 178502733, compoundYield 46.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Cis-4-hydroxycyclohexanecarboxylic acid (6 g, 0.042 mol) and EDCI (9.6 g, 0.05 mol, 1.2 eq.) were dissolved in DCM (100 mL) at 0° C. and stirred for 10 min. DIPEA (16 mL, 0.126 mol, 3.0 eq.) and N,O-dimethylhydroxylamine hydrochloride (4.44 g, 0.046 mol, 1.1 eq.) were added to the mixture at 0° C. The mixture was warmed to room temperature and stirred for 15 h., water was added and the mixture was extracted with DCM. The organic layer was concentrated and purified by silica gel column chromatography using DCM/CH3OH (10/1) to give product as a colorless oil (3.685 g, 40%). 1H NMR (400 MHz, CDCl3) δ: 4.01 (s, 1H), 3.70 (s, 3H), 3.18 (s, 3H), 2.72-2.69 (m, 1H), 1.98-1.85 (m, 4H), 1.62-1.55 (m, 4H).

Workup

  1. stirringstirred for 15 h.
  2. extractionthe mixture was extracted with DCM
  3. concentrationThe organic layer was concentrated
  4. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-32e50feee698453e99d610389db7d9aa
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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