Butanal → 1-Butyl-2-ethoxycarbonyl-3-propylaziridine

HRID 430845Notes

Reaction equation

HRID 430845 reaction equation
[CH:1](=O)[CH2:2][CH2:3][CH3:4].[CH2:6]([NH2:10])[CH2:7][CH2:8][CH3:9].[N+](=[CH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N-]>O1CCCC1>[CH2:6]([N:10]1[CH:1]([CH2:2][CH2:3][CH3:4])[CH:13]1[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 261ButanalHCID 8007ButylamineHCID 12192Ethyl diazoacetate

Product 1

HCID 98157521-Butyl-2-ethoxycarbonyl-3-propylaziridineYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-5 °C

Procedure

A small amount of a molecular sieve was added to a mixture of 0.5 mmol of n-butyraldehyde, 0.5 mmol of butylamine, 1 mmol of ethyl diazoacetate, 0.025 mmol of di-l-chlorobis(1,5-cyclooctadiene)diiridium(I) [Ir2Cl2(cod)2], and 0.5 ml of tetrahydrofuran. The resulting mixture was stirred at −5° C. in an argon atmosphere for 3 hours to yield 1-butyl-2-ethoxycarbonyl-3-propylaziridine in a yield of 74%.

Sources & evidence

ORD record
ord-0082dfbc703e474f946fa8f10967734a
Source dataset
uspto-grants-2001_11
Patent number
US06323346B1

Reaction notes

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