1,5-Dibromopentane → HCID 11333205, compound

HRID 356643

Reaction equation

HRID 356643 reaction equation
[C:1]1([C@H:7]([CH2:9][OH:10])[NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]Br.C([O-])([O-])=O.[K+].[K+]>C(O)C.C(Cl)Cl>[N:8]1([C@H:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:9][OH:10])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 81001,5-DibromopentaneHCID 11430Potassium CarbonateHCID 2724025(R)-beta-aminophenethyl alcohol

Product 1

HCID 11333205HCID 11333205, compoundYield 138.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension mixture of (R)-(-)-2-phenylglycinol(686 mg, 5 mmol), 1,5-dibromopentane (0.82 ml, 6 mmol), and K2CO3 (1.38 g, 10 mmol) in ethanol (15 ml) was refluxed with stirring for 23 h. After cooling down to rt, the white solid was removed by filtration and the filtrate was concentrated to give white solid oil mixture. This was suspended in CH2Cl2 (30 ml), washed with water and saturated NaHCO3 aqueous solution, dried (Na2SO4), and concentrated to give 1.42 g of clear yellow oil. This was purified by column chromatography (silica gel: 50 g, CH2Cl1 /MeOH:30/1 to 20/1) to afford 955 mg (93%) of desired compound as clear light yellow oil.

Workup

  1. temperaturewas refluxed
  2. customthe white solid was removed by filtration
  3. concentrationthe filtrate was concentrated
  4. customto give white solid oil mixture
  5. washwashed with water and saturated NaHCO3 aqueous solution
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-22206538a3d8469da3f1db0fed58bfb5
Source dataset
uspto-grants-1998_11
Patent number
US05837717

Linked notes

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