1,3-Dibromopropane → HCID 131732140, compound

HRID 1400077Notes

Reaction equation

HRID 1400077 reaction equation
[CH3:1][C:2]1[N:3]([CH:8]2[CH2:12][C@H:11]([C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:14])[CH:10]=[CH:9]2)[C:4]([CH3:7])=[CH:5][CH:6]=1.[Br:23][CH2:24][CH2:25][CH2:26]Br>O1CCCC1>[Br:23][CH2:24][CH2:25][CH2:26][C@@:11]1([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:12][C@H:8]([N:3]2[C:2]([CH3:1])=[CH:6][CH:5]=[C:4]2[CH3:7])[CH:9]=[CH:10]1

Participants

4

Reactant 2

HCID 80011,3-DibromopropaneHCID 131732141HCID 131732141, compound

Product 1

HCID 131732140HCID 131732140, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of Example 48A (21.94 g, 74.4 mmol) in tetrahydrofuran (200 ml) was added dropwise lithium hexamethyl bis(trimethylsilyl)amide (1 M in tetrahydrofuran, 119 mL) at −50° C. The reaction mixture was stirred for 1 hour at the same temperature. 1,3-dibromopropane (150 g, 744 mmol) was added dropwise over 1 hour. The reaction mixture was allowed to warm to −20° C. and stirred at the same temperature for 1 hour. LCMS showed that the reaction was complete. The reaction mixture was quenched with an aqueous ammonium chloride solution (6%, 600 mL), and extracted with ethyl acetate. The organic fraction was washed with aqueous ammonium chloride (6%), brine, dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography (petroleum ether:ethyl acetate=80:1) to give the title compound.

Workup

  1. stirringstirred at the same temperature for 1 hour
  2. customThe reaction mixture was quenched with an aqueous ammonium chloride solution (6%, 600 mL)
  3. extractionextracted with ethyl acetate
  4. washThe organic fraction was washed with aqueous ammonium chloride (6%), brine
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography (petroleum ether:ethyl acetate=80:1)

Sources & evidence

ORD record
ord-8dbb0f56105d479ea5b14452b1ef8bdb
Source dataset
uspto-grants-2014_12
Patent number
US08906911B2

Reaction notes

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