Triethylamine → HCID 67132987, compound

HRID 2421805Notes

Reaction equation

HRID 2421805 reaction equation
[O:1]=[C:2]([O:8][C@H:9]1[CH2:14][C@@H:13]2[C:15]([CH3:17])([CH3:16])[C@@:10]1(C)[CH2:11][CH2:12]2)[CH2:3][CH2:4][C:5]([OH:7])=[O:6].[CH:19]1[CH:24]=[CH:23][C:22]([CH:25](O)CNC2N=CC=CC=2)=[CH:21][CH:20]=1.Cl.[CH2:36](N(CC)CC)C>CC(OC)(C)C>[C:5]([O:7][CH2:25][C:22]1[CH:23]=[CH:24][CH:19]=[CH:20][CH:21]=1)(=[O:6])[CH2:4][CH2:3][C:2]([O:8][CH:9]1[CH2:14][CH:13]([CH3:36])[CH:12]2[CH2:11][CH:10]1[C:15]2([CH3:16])[CH3:17])=[O:1]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9469326-43-2HCID 671330801-[(1R,2S,4R)-1,7,7-Trimethylbicyclo[2.2.1]hept-2-yl] butanedioate

Product 1

HCID 67132987HCID 67132987, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
40 °C

Procedure

Benzyl-4-chloro-4-oxobutanoate (3.22 g, 1 eq, from Example 2) was dissolved in MTBE (100 mL) in a 300 mL round bottom flask. Verbanol™ (2.12 g, 1 eq) and triethylamine (1.39 g, 1 eq) were added and the reaction was heated at 40° C. and stirred overnight. The reaction mixture was extracted with a dual-layer MTBE-1N HCl system. The organic layer was washed with brine, dried over MgSO4 and concentrated. Toe crude product was purified using column chromatography to give 3.45 g of a clear oil (73%).

Workup

  1. extractionThe reaction mixture was extracted with a dual-layer MTBE-1N HCl system
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customToe crude product was purified

Sources & evidence

ORD record
ord-a2d2d4200221464cac1fe5d964a612bc
Source dataset
uspto-grants-2011_06
Patent number
US07959958B2

Reaction notes

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