3-Methyl-5-(trichloromethyl)-1,2,4-oxadiazole → (R,R)-2-(tert-Butyloxycarbonyl)-5-(3-methyl-1,2,4-oxadiazol-5-yl)-2,5-diazabicyclo[2.2.1]heptane

HRID 2260803Notes

Reaction equation

HRID 2260803 reaction equation
[CH3:1][C:2]1[N:6]=[C:5](C(Cl)(Cl)Cl)[O:4][N:3]=1.[C:11]([O:15][C:16]([N:18]1[CH2:23][C@H:22]2[CH2:24][C@@H:19]1[CH2:20][NH:21]2)=[O:17])([CH3:14])([CH3:13])[CH3:12]>C1(C)C=CC=CC=1>[C:11]([O:15][C:16]([N:18]1[CH2:23][C@H:22]2[CH2:24][C@@H:19]1[CH2:20][N:21]2[C:5]1[O:4][N:3]=[C:2]([CH3:1])[N:6]=1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

4

Reactant 2

HCID 709533-Methyl-5-(trichloromethyl)-1,2,4-oxadiazoleHCID 11860399N-Boc-2,5-diazabicyclo[2.2.1]heptane

Product 1

HCID 15813431(R,R)-2-(tert-Butyloxycarbonyl)-5-(3-methyl-1,2,4-oxadiazol-5-yl)-2,5-diazabicyclo[2.2.1]heptaneYield 50.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 1.06 g of 3-methyl-5-trichloromethyl-1,2,4-oxadiazole prepared by the procedure of F. Eloy, Bull. Soc. Chim. Belg., 1964, 73, 793, in 2 ml of toluene is added slowly to a solution of 1.05 g of product from Example 1 and 0.82 g of diazabicyclo[3.6.0]unodecene-5 in 1 ml of toluene. The resulting mixture is stirred at room temperature for 3 days and then concentrated in vacuo to dryness. The residue is purified by chromatography (aluminum oxide, Activity Grade 2.5; methylene chloride) to give 0.74 g of the desired product as an off-white solid:

Workup

  1. concentrationconcentrated in vacuo to dryness
  2. customThe residue is purified by chromatography (aluminum oxide, Activity Grade 2.5; methylene chloride)

Sources & evidence

ORD record
ord-1aca56a49d85464f82e2e249e9516da2
Source dataset
uspto-grants-1995_12
Patent number
US05478939

Reaction notes

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