Benzyl Bromide → HCID 68578703, compound

HRID 639508Notes

Reaction equation

HRID 639508 reaction equation
[C:1]([N:8]1[CH2:31][CH2:30][C@@:15]23[C:16]4[CH:17]=[C:18]([O:23][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])[CH:19]=[CH:20][C:21]=4[CH2:22][C@@H:9]1[C@@H:10]2[CH2:11][CH2:12][CH2:13][CH2:14]3)(OC(C)(C)C)=O.O1CCOCC1.Cl.C(Br)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C(Cl)Cl>[CH2:1]([N:8]1[CH2:31][CH2:30][C@@:15]23[C:16]4[CH:17]=[C:18]([O:23][C:24](=[O:29])[C:25]([CH3:27])([CH3:26])[CH3:28])[CH:19]=[CH:20][C:21]=4[CH2:22][C@@H:9]1[C@@H:10]2[CH2:11][CH2:12][CH2:13][CH2:14]3)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 204431481,4-Dioxane hydrochlorideHCID 59254992HCID 59254992, compound

Product 1

HCID 68578703HCID 68578703, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of compound 31 (5 mg, 0.012 mmol) in dry CH2Cl2 (0.2 ml) was added 4 M HCl dioxane solution (0.5 mL) and the mixture stirred for 2 h at 0° C. Solvent was evaporated under reduced pressure. The crude amine salt 32 was dissolved in CH2Cl2 (0.5 ml) and to it were slowly added benzyl bromide (2 μL, 0.020 mmol) and TEA (9 μL, 0.064 mmol) at 0° C. After 4 h stirring, the reaction mixture was concentrated under reduced pressure. The crude product was purified on a silica gel column chromatography (3:1 n-Hexane/EtOAc) to give a colorless oil (4 mg, 80% yield): 1H NMR (300 MHz, CDCl3) 0.91˜1.74 (m, 18H); 1.89 (m, J=12.6 Hz, 1H); 2.07˜2.21 (m, 1H), 2.29˜2.48 (m, 2H); 2.63˜2.69 (m, 1H); 2.87 (s, 1H); 3.09 (d, J=18.3 Hz, 1H); 3.68 (dd, J=13.4 Hz, 2H); 6.82˜6.93 (m, 2H); 7.15 (d, J=8.3 Hz, 1H); 7.25˜7.38 (m, 5H).

Workup

  1. customSolvent was evaporated under reduced pressure
  2. dissolutionThe crude amine salt 32 was dissolved in CH2Cl2 (0.5 ml) and to it
  3. customat 0° C
  4. stirringAfter 4 h stirring
  5. concentrationthe reaction mixture was concentrated under reduced pressure
  6. customThe crude product was purified on a silica gel column chromatography (3:1 n-Hexane/EtOAc)

Sources & evidence

ORD record
ord-209a8d3082ae4f239be6c9240f827c97
Source dataset
uspto-grants-2010_04
Patent number
US07691874B2

Reaction notes

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