Allyl bromide → (R)-N-Allyl-1-aminoindane

HRID 1038988Notes

Reaction equation

HRID 1038988 reaction equation
[C@H:1]1([NH2:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH2:18](Br)[CH:19]=[CH2:20]>C(Cl)Cl>[CH2:20]([NH:10][C@H:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1)[CH:19]=[CH2:18]

Participants

5

Reactant 3

HCID 7841Allyl bromide2×HCID 8471Triethylamine2×HCID 2733933(R)-(-)-1-Aminoindan

Product 1

HCID 5326779(R)-N-Allyl-1-aminoindane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1R)-indan-1-amine (1.00 g, 7.51 mmol) and triethylamine (1.52 g, 15.0 mmol) in DCM (75 mL) was added allyl bromide (1.36 g, 11.3 mmol) and the mixture was allowed to stir at ambient temperature for 3 days. An additional 1.5 equivalents of allyl bromide and 0.5 equivalents of triethylamine were then added, and the reaction mixture was stirred an additional 24 hours. LCMS analysis now indicates the reaction mixture is a 27:35:38 mixture of starting material:desired product:bis-allylation product. Use this solution as is.

Workup

  1. stirringthe reaction mixture was stirred an additional 24 hours
  2. additiona 27:35:38 mixture of starting material

Sources & evidence

ORD record
ord-53dbdc49b1614eab9da7af2681f00f5a
Source dataset
uspto-grants-2013_10
Patent number
US08552023B2

Reaction notes

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