Triethylamine → HCID 2475880, compound

HRID 2307664Notes

Reaction equation

HRID 2307664 reaction equation
[O:1]([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C.[C@@H:28]1([NH2:38])[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH2:31][CH2:30][CH2:29]1>C(Cl)Cl>[O:1]([CH2:8][CH2:9][CH2:10][C:11]([NH:38][C@@H:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH2:31][CH2:30][CH2:29]1)=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 227414-Phenoxybutyric acidHCID 62493Pivaloyl chlorideHCID 70580741-Aminotetralin, (S)-

Product 1

HCID 2475880HCID 2475880, compoundYield 115.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Phenoxybutanoic acid (1.05 g, 5.8 mmol, Lancaster) and triethylamine (2.4 mL, 17.4 mmol) in anhydrous CH2Cl2 (25 mL) were treated with pivaloyl chloride (0.75 mL, 6.1 mmol) at 0° C. After stirring for 1 hour, the reaction mixture was treated with (1S)-1,2,3,4-tetrahydro-1-naphthalenylamine (1.0 mL, 6.9 mmol) and the reaction mixture was allowed to warm to room temperature and stir for 16 hours. The reaction mixture was diluted with CH2Cl2, washed with 1N HCl, saturated NaHCO3, brine, dried (Na2SO4), filtered and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, 40% ethyl acetate/hexanes) to provide the title compound as a colorless oil (2.07 g).

Workup

  1. stirringstir for 16 hours
  2. washwashed with 1N HCl, saturated NaHCO3, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (silica gel, 40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-d6e841da843b4e15a2ec1ab8704f6f5d
Source dataset
uspto-grants-2004_12
Patent number
US06831193B2

Reaction notes

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