Triethylamine → HCID 15431014, compound

HRID 2305824Notes

Reaction equation

HRID 2305824 reaction equation
C(N(CC)CC)C.[C:8]([C:10]1([C:17]([OH:19])=O)[C:12]([CH3:14])([CH3:13])[C:11]1([CH3:16])[CH3:15])#[N:9].[CH:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][C:21]=1[C@H:30]([NH2:32])[CH3:31].C(P(=O)(OCC)OCC)#N>ClCCl>[C:8]([C:10]1([C:17]([NH:32][C@@H:30]([C:21]2[CH:22]=[CH:23][C:24]3[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:20]=2)[CH3:31])=[O:19])[C:11]([CH3:15])([CH3:16])[C:12]1([CH3:13])[CH3:14])#[N:9]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 1798835(1R)-1-(naphthalen-2-yl)ethan-1-amineHCID 15431013HCID 15431013, compound

Product 1

HCID 15431014HCID 15431014, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.61 g (6 mmol) of triethylamine was added to a solution of 1.0 g (6 mmol) of 1-cyano-2,2,3,3-tetramethylcyclopropane-1-carboxylic acid (cf. Org. Prep. Proced. Int. 5, (1973), 25-29) and 1.03 g (6 mmol) of (1 R)-1-naphth-2-ylethylamine in 50 ml of dichloromethane. At 10° C., 0.94 g of 93% pure diethyl cyanophosphonate (6 mmol) was then added dropwise, and the mixture was stirred at room temperature for 12 hours. The reaction solution was concentrated using a rotary evaporator and then purified by silica gel chromatography (mobile phase: methyl tert-butyl ether:hexane=1:9, then 3:7). 1.9 g (99% yield) of the title compound were isolated as a white solid of melting point 169-1750° C.

Workup

  1. concentrationThe reaction solution was concentrated
  2. customa rotary evaporator
  3. custompurified by silica gel chromatography (mobile phase

Sources & evidence

ORD record
ord-c25ca0ef9dd44d71919fd529168615da
Source dataset
uspto-grants-2002_08
Patent number
US06441044B1

Reaction notes

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