1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 59605224, compound

HRID 1922726Notes

Reaction equation

HRID 1922726 reaction equation
[NH:1]1[CH2:5][CH2:4][C@@H:3]([OH:6])[CH2:2]1.[C:7]([O:11][C:12]([N:14]1[CH2:17][CH:16]([C:18](O)=[O:19])[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].Cl.CN(C)CCCN=C=NCC>ClCCl>[C:7]([O:11][C:12]([N:14]1[CH2:17][CH:16]([C:18]([N:1]2[CH2:5][CH2:4][C@@H:3]([OH:6])[CH2:2]2)=[O:19])[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27559811-Boc-Azetidine-3-carboxylic acidHCID 2759337(R)-3-Pyrrolidinol

Product 1

HCID 59605224HCID 59605224, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(R)-Pyrrolidin-3-ol (0.276 g, 3.17 mmol) was added to a mixture of azetidine-1,3-dicarboxylic acid mono-tert-butyl ester (0.4 g, 2.11 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.61 g, 3.17 mmol) in dichloromethane (7 mL). The resulting reaction mixture was stirred at RT under nitrogen atmosphere for 18 h. The mixture was diluted with DCM (10 mL) and washed with water (1×15 mL), 10% aqueous citric acid solution (2×15 mL) and brine (2×15 mL), and dried over sodium sulfate. The solvents were reduced in vacuo to afford the title compound as colourless oil (0.42 g, 74%). 1H NMR (400 MHz, CDCl3): δ 4.54-4.52 (1 H, m), 4.11-4.09 (4 H, m), 3.50-3.48 (5 H, m), 2.01-2.00 (2 H, m), 1.43 (9 H, d, J=0.78 Hz)

Workup

  1. customThe resulting reaction mixture
  2. washwashed with water (1×15 mL), 10% aqueous citric acid solution (2×15 mL) and brine (2×15 mL)
  3. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-452f8be06de34e78bbcfd1b34fd58eb4
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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