Triethylamine → N-(2-(1H-inden-3-yl)ethyl)-7,7-dimethyl-2-oxobicyclo(2.2.1)heptane-1-methanesulfonamide

HRID 1534798Notes

Reaction equation

HRID 1534798 reaction equation
[CH:1]1([CH2:10][CH2:11][NH2:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[CH3:13][C:14]1([CH3:27])[C:18]2([CH2:22][S:23](Cl)(=[O:25])=[O:24])[C:19]([CH2:21][CH:15]1[CH2:16][CH2:17]2)=[O:20].C(N(CC)CC)C>C(Cl)Cl>[CH2:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:1]([CH2:10][CH2:11][NH:12][S:23]([CH2:22][C:18]23[C:14]([CH3:13])([CH3:27])[CH:15]([CH2:16][CH2:17]2)[CH2:21][C:19]3=[O:20])(=[O:25])=[O:24])=[CH:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 26579910-Camphorsulfonyl chlorideHCID 19908306(2-(1H-Indene-1-yl)ethyl)amine

Product 1

HCID 19908305N-(2-(1H-inden-3-yl)ethyl)-7,7-dimethyl-2-oxobicyclo(2.2.1)heptane-1-methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2-(1H-Indene-1-yl)ethyl)amine (190 mg, 1.19 mmol) and (+)-10-camphorsulfonyl chloride (299 mg, 1.19 mmol) were combined in CH2Cl2 (2 ml), treated with triethylamine (87 μl, 120 mg, 1.19 mmol), and the mixture was stirred at ambient temperature overnight. The mixture was chromatographed on a silica gel column eluted with 25% EtOAc in hexane and the product fractions were evaporated to dryness in vacuo to give N-(2-(1H-inden-3-yl)ethyl)-7,7-dimethyl-2-oxobicyclo(2.2.1)heptane-1-methanesulfonamide.

Workup

  1. customThe mixture was chromatographed on a silica gel column
  2. washeluted with 25% EtOAc in hexane
  3. customthe product fractions were evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-6c839ea95a5749fba2b34138b6a059f8
Source dataset
uspto-grants-1992_02
Patent number
US05091387

Reaction notes

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