Dichloromethane → HCID 70131009, compound

HRID 1936969Notes

Reaction equation

HRID 1936969 reaction equation
Br.[C:2]1([C@H:8]([NH:10][C@@H:11]2[CH2:17][CH2:16][CH2:15][C:14]3[CH:18]=[CH:19][C:20]([OH:22])=[CH:21][C:13]=3[CH2:12]2)[CH3:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].C(=O)([O-])[O-].[K+].[K+].[Cl:36]CCl>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[ClH:36].[C:2]1([C@H:8]([NH:10][C@@H:11]2[CH2:17][CH2:16][CH2:15][C:14]3[CH:18]=[CH:19][C:20]([O:22][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:21][C:13]=3[CH2:12]2)[CH3:9])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 70130125HCID 70130125, compound

Product 1

HCID 70131009HCID 70131009, compound

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of N-((R)-1-phenylethyl)-((6R)-3-hydroxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amine-hydrobromide (7.67 g), ethyl bromoacetate (3.8 ml), potassium carbonate (17.6 g), and tetrabutylammonium chloride (1.18 g) in a mixture of dichloromethane (80 ml) and water (40 ml) was refluxed for 9 hours. After separation, the organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was dissolved in ethyl acetate (90 ml). To the solution was added 4N hydrogen chloride in ethyl acetate (5.6 ml), and the mixture was stirred at 5° C. for 1 hour. The precipitate was collected, washed with a little amount of ice-cold ethyl acetate, and dried under reduce pressure to afford N-((R)-1-phenylethyl)-((6R)-3-ethoxycarbonylmethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amine hydrochloride (4.99 g).

Workup

  1. temperaturewas refluxed for 9 hours
  2. customAfter separation
  3. washthe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated in vacuo
  6. dissolutionThe residue was dissolved in ethyl acetate (90 ml)
  7. additionTo the solution was added 4N hydrogen chloride in ethyl acetate (5.6 ml)
  8. customThe precipitate was collected
  9. washwashed with a little amount of ice-cold ethyl acetate
  10. customdried

Sources & evidence

ORD record
ord-86681d99fb8241f382cbb86cff18afce
Source dataset
uspto-grants-2002_05
Patent number
US06391915B2

Reaction notes

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