Bromocycloheptane → HCID 69651826, compound

HRID 2213547Notes

Reaction equation

HRID 2213547 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]#[C:5][CH2:6][O:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2.[CH:19]1([N:26]=[N+:27]=[N-:28])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.C1(Br)CCCCCC1.[N-]=[N+]=[N-].[Na+]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([C:4]1[N:26]([CH:19]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[N:27]=[N:28][C:5]=1[CH2:6][O:7][C:8]12[CH2:17][CH:12]3[CH2:11][CH:10]([CH2:16][CH:14]([CH2:13]3)[CH2:15]1)[CH2:9]2)=[O:18]

Participants

6

Reactant 4

HCID 16992BromocycloheptaneHCID 33557Sodium AzideHCID 14917746HCID 14917746, compoundHCID 69651915HCID 69651915, compound

Product 1

HCID 69651826HCID 69651826, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of the product from step b (2.74 g, 11.1 mmol) and cycloheptyl azide (prepared by the reaction of cycloheptyl bromide and sodium azide) (1.54 g, 11.1 mmol) in toluene (14 ml) was heated under reflux for 42 hours. The solvent was removed invacuo and the residue purified by flash column chromatography (hexane:EtOAc 3:1) to yield 5-(adamantan-1-yloxymethyl)-3-cycloheptyl-3H-[1,2,3]triazole-4-carboxylic acid methyl ester (1.53 g, 36%). 1H NMR (CDCl3) 5.27-5.21 (1H, m), 4.73 (2H, s), 3.94 (3H, s), 2.20-2.11 (7H, m), 1.86-1.85 (8H, m), 1.69-1.60 (12H, m). Further eluation gave rise to 5-(adamantan-1-yloxymethyl)-1-cycloheptyl-1H-[1,2,3]triazole-4-carboxylic acid methyl ester (2.00 g, 47%). 1H NMR (CDCl3) 4.93 (2H, s), 4.74-4.65 (1H, m), 3.94 (3H, s), 2.32-2.04 (8H, m), 2.00-1.54 (19H, m).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 42 hours
  3. customThe solvent was removed invacuo
  4. customthe residue purified by flash column chromatography (hexane:EtOAc 3:1)

Sources & evidence

ORD record
ord-3b345674b08c4515923ca6beeb2d1cd3
Source dataset
uspto-grants-2006_09
Patent number
US07105558B2

Reaction notes

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