Triethylamine → HCID 28431656, compound

HRID 1891265Notes

Reaction equation

HRID 1891265 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH2:10])[CH3:9])=[CH:4][CH:3]=1.Br[CH2:12][C:13]([O:15][CH3:16])=[O:14].C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:10][CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 60984Methyl bromoacetateHCID 853000(R)-4-bromo-alpha-methylbenzylamine

Product 1

HCID 28431656HCID 28431656, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

(R)-1-(4-Bromophenyl)ethanamine (6G1) (2.10 mmol, 419 mg), methyl 2-bromoacetate (6G2) (2.10 mmol, 320 mg) and triethylamine (4.19 mmol, 424 mg) were dissolved in DCM (3 ml) and heated in the microwave at 120° C. for 20 min. The crude mixture was concentrated before purification on silica eluting with 20% EtOAc/heptane to give (R)-methyl 2-(1-(4-bromophenyl)ethylamino)acetate (6G3) 230 mg (40.1%); 1H NMR (400 MHz, CDCl3) δ 7.44 (d, 2H) 7.20 (d, 2H) 3.77 (q, 1H) 3.69 (s, 3H) 3.4-3.18 (dd, 2H) 1.34 (d, 3H)

Workup

  1. concentrationThe crude mixture was concentrated before purification on silica eluting with 20% EtOAc/heptane

Sources & evidence

ORD record
ord-068e37736d934174affc492beb15b830
Source dataset
uspto-grants-2013_08
Patent number
US08507521B2

Reaction notes

Loading…