Methyl 4-bromobutyrate → HCID 69002319, compound

HRID 2103314Notes

Reaction equation

HRID 2103314 reaction equation
[CH2:1]([C:8]1[CH:19]=[CH:18][C:11]([O:12][C@@H:13]2[CH2:17][CH2:16][NH:15][CH2:14]2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][O:21][C:22](=[O:27])[CH2:23][CH2:24][CH2:25]Br>C(Cl)Cl.C(N(CC)CC)C>[CH3:20][O:21][C:22](=[O:27])[CH2:23][CH2:24][CH2:25][N:15]1[CH2:16][CH2:17][C@@H:13]([O:12][C:11]2[CH:18]=[CH:19][C:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:9][CH:10]=2)[CH2:14]1

Participants

5

Reactant 2

HCID 107604Methyl 4-bromobutyrateHCID 24883113HCID 24883113, compound

Product 1

HCID 69002319HCID 69002319, compoundYield 40.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a solution of (R)-3-(4-Benzyl-phenoxy)-pyrrolidine (126 mg, 0.5 mmol) in anhydrous CH2Cl2 (0.5 mL) was added methyl-4-bromobutyrate (99 mg, 0.55 mmol) in CH2Cl2 (0.5 mL) and triethylamine (101 mg, 1.0 mmol. The resulting mixture was purged with nitrogen and stirred at rt for 16 h. CH2Cl2 was removed in vacuo and crude mixture was partioned between EtOAc and water. EtOAc layer was removed, washed with brine, dried over anhydrous MgSO4 and concentrated. The crude mixture was purified by silica gel flash chromatography (40% EtOA /Hexane) to obtain the product as yellow solid (71 mg, 40%): MS; m/z 354.5 (M+H); 1H NMR (400 MHz, DMSO-d6); δ 1.65-1.72 (m, 2H), 2.18-2.39 (m, 4H), 2.54-2.63 (m, 5H), 2.78-2.82 (m, 1H), 3.57 (s, 3H), 3.85 (s, 2H), 5.78 (m, 1H), 6.78 (d, 2H, J=8.8 Hz), 7.11 (d, 2H, J=8.4Hz), 7.16-7.29 (m, 5H); HPLC (ELSD); 99%.

Workup

  1. customThe resulting mixture was purged with nitrogen
  2. customCH2Cl2 was removed in vacuo and crude mixture
  3. customEtOAc layer was removed
  4. washwashed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated
  7. customThe crude mixture was purified by silica gel flash chromatography (40% EtOA /Hexane)

Sources & evidence

ORD record
ord-37f12384c4bd4a94960b62d38e775f94
Source dataset
uspto-grants-2009_08
Patent number
US07576102B2

Reaction notes

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