Triethylamine → HCID 85524729, compound

HRID 1982626Notes

Reaction equation

HRID 1982626 reaction equation
[CH3:1][CH:2]([CH3:7])[CH2:3][C@H:4]1[CH2:6][NH:5]1.C(N(CC)CC)C.Cl[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]>CCOCC>[CH3:1][CH:2]([CH3:7])[CH2:3][CH:4]1[CH2:6][N@@:5]1[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 12695796(2S)-2-(2-Methylpropyl)aziridine

Product 1

HCID 85524729HCID 85524729, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 24.3 g of (S)-2-(2-methylpropyl)aziridine [Bull. Chem. Soc. (Japan) 35, 1004 (1962).] in 500 ml of ether is treated with 34.2 ml of triethylamine and cooled in ice. While stirring rapidly 40.4 ml (a 10% excess) of benzyl chloroformate is added dropwise over a 30 minute period. After stirring for one hour at 0°, the triethylamine, hydrochloride is filtered off and the ether removed under reduced pressure. The residue is distilled under reduced pressure. After a forerun of benzyl chloride, the product distills at 105°-122°/0.6 mm. There is obtained 51.66 g (90.5% yield) of (S)-2-(2-methylpropyl)-1-aziridinecarboxylic acid, phenylmethyl ester.

Workup

  1. temperaturecooled in ice
  2. additionis added dropwise over a 30 minute period
  3. filtrationthe triethylamine, hydrochloride is filtered off
  4. customthe ether removed under reduced pressure
  5. distillationThe residue is distilled under reduced pressure
  6. distillationAfter a forerun of benzyl chloride, the product distills at 105°-122°/0.6 mm

Sources & evidence

ORD record
ord-4f27b4938d1342fd898ea8b7914af2ab
Source dataset
uspto-grants-1986_06
Patent number
US04596819

Reaction notes

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