Allyl bromide → HCID 68576964, compound

HRID 2390911Notes

Reaction equation

HRID 2390911 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([OH:14])[CH2:9][NH:10][CH2:11][CH2:12][OH:13])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:22](Br)[CH:23]=[CH2:24]>CC(N(C)C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([OH:14])[CH2:9][N:10]([CH2:11][CH2:12][OH:13])[CH2:24][CH:23]=[CH2:22])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 8471TriethylamineHCID 51890492HCID 51890492, compound

Product 1

HCID 68576964HCID 68576964, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
25 °C

Procedure

To (R)-1-(4-chlorophenyl)-2-[(2-hydroxyethyl)amino]-1-ethanol (755 mg, 3.5 mmol) produced in Example 12, dimethylacetamide (5 mL), triethylamine (532 mg, 1.5 equivalents) and allyl bromide (508 mg, 1.2 equivalents) were added. The mixture was stirred at 25° C. for 16 hours. Toluene (5 mL) and distilled water (5 mL) were added to the mixture, and the organic layer and aqueous layer were separated. The organic layer was washed twice with distilled water (5 mL), then concentrated and dried under vacuum, to obtain 817 mg of the title compound as colorless oil (yield: 79%, chemical purity: 92.2 area %). The retention time in the chemical purity analysis method was 2.0 min.

Workup

  1. distillationToluene (5 mL) and distilled water (5 mL)
  2. additionwere added to the mixture
  3. customthe organic layer and aqueous layer were separated
  4. washThe organic layer was washed twice with distilled water (5 mL)
  5. concentrationconcentrated
  6. customdried under vacuum

Sources & evidence

ORD record
ord-d16eaf2be54b4e64a4f9b24b6aaacada
Source dataset
uspto-grants-2012_09
Patent number
US08273883B2

Reaction notes

Loading…