(3-Bromopropyl)benzene → HCID 59371626, compound

HRID 2095434Notes

Reaction equation

HRID 2095434 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:14][CH2:13][C@@H:12]([CH2:15][OH:16])[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].Br[CH2:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1.[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-]>[C:21]1([CH2:20][CH2:19][CH2:18][O:16][CH2:15][C@@H:12]2[CH2:13][CH2:14][N:10]([C:8]([O:7][C:3]([CH3:6])([CH3:5])[CH3:4])=[O:9])[CH2:11]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 12503(3-Bromopropyl)benzeneHCID 24758Sodium hydrideHCID 1514340tert-Butyl (3R)-3-(hydroxymethyl)pyrrolidine-1-carboxylate

Product 1

HCID 59371626HCID 59371626, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

NaH (170 mg, 7.1 mmol, 2.0 equiv.) was added to a solution of 1-(tert-butoxycarbonyl)-3(R)-pyrrolidinylmethanol (500 mg, 2.49 mmol) in anhydrous THF (40 mL) with ice cooling under N2. The solution was stirred for 2 h at room temperature. (3-Bromopropyl)benzene (590 mg, 2.96 mmol, 1.2 equiv.) and n-Bu4NBr (80 mg, 0.25 mmol, 0.10 equiv.) were added, and the mixture was stirred overnight at 25° C. The reaction was then quenched with water. After concentration under vacuum, the solution was extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was applied onto a silica gel column, which was eluted with EtOAc/petroleum ether 1:10 to afford the product (500 mg, 63%) as a yellowish oil. 1H NMR (CDCl3, 300 MHz) δ 7.33-7.19 (m, 5H), δ 3.55-3.31 (m, 7H), δ 3.11 (dd, 1H, J=10.8, 6.9 Hz), 2.71 (t, 2H) 2.48 (m, 1H), 1.87-2.01 (m, 3H), 1.71-1.64 (m, 1H), 1.48 (s, 9H). LC-MS (ESI) m/z 320 (M+H+).

Workup

  1. stirringthe mixture was stirred overnight at 25° C
  2. customThe reaction was then quenched with water
  3. concentrationAfter concentration under vacuum
  4. extractionthe solution was extracted with EtOAc
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. washwas eluted with EtOAc/petroleum ether 1:10

Sources & evidence

ORD record
ord-d07e0a4b5e20447f95cb5c462cbae4c0
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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