Phenethyl bromide → HCID 67071414, compound

HRID 874245Notes

Reaction equation

HRID 874245 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:22])/[CH:5]=[CH:6]/[C:7]1[CH:8]=[C:9]2[C:18](=[CH:19][CH:20]=1)[O:17][C:12]1([CH2:16][CH2:15][NH:14][CH2:13]1)[CH2:11][C:10]2=[O:21].CCN(C(C)C)C(C)C.[CH2:32](Br)[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C(Cl)Cl>[CH3:2][O:3][C:4](=[O:22])/[CH:5]=[CH:6]/[C:7]1[CH:8]=[C:9]2[C:18](=[CH:19][CH:20]=1)[O:17][C:12]1([CH2:16][CH2:15][N:14]([CH2:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH2:13]1)[CH2:11][C:10]2=[O:21]

Participants

5

Reactant 3

HCID 7666Phenethyl bromideHCID 81531DiisopropylethylamineHCID 67071652HCID 67071652, compound2×

Product 1

HCID 67071414HCID 67071414, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of (E)-3-[4-oxo-spiro(chromane-2,3′-pyrrolidine)-6-yl]-acrylic acid methyl ester (500 mg, 1.55 mmol, Intermediate 1) in DCM (15 ml) was treated with DIPEA (0.33 ml, 1.86 mmol) and phenethyl bromide (0.251 ml, 1.86 mmol), and stirred at RT for 8 days. The mixture was concentrated and the crude residue was purified by column chromatography (eluent: petroleum ether/EtOAc 7:3) to give (±)-(E)-3-[1′-(2-phenyl-ethyl)-4-oxo-spiro(chromane-2,3′-pyrrolidine)-6-yl]-acrylic acid methyl ester a yellow solid (280 mg).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe crude residue was purified by column chromatography (eluent: petroleum ether/EtOAc 7:3)

Sources & evidence

ORD record
ord-8a4b2177e5544a27965d30ed6921d760
Source dataset
uspto-grants-2015_03
Patent number
US08980877B2

Reaction notes

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