ethyl (S)-3-[2-(tert-butoxycarbonylamino)-1,2,3,4-tetrahydronaphthalen-7-yl]acrylate → ethyl (S)-3-[2-(tert-butoxycarbonylamino)-1,2,3,4-tetrahydronaphthalen-7-yl]propionate

HRID 369362Notes

Reaction equation

HRID 369362 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][C:13]([CH:19]=[CH:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:14][CH:15]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][C:13]([CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:14][CH:15]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 57134535ethyl (S)-3-[2-(tert-butoxycarbonylamino)-1,2,3,4-tetrahydronaphthalen-7-yl]acrylate

Product 1

HCID 57250977ethyl (S)-3-[2-(tert-butoxycarbonylamino)-1,2,3,4-tetrahydronaphthalen-7-yl]propionateYield 93.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Ethyl (S)-3-[2-(tert-butoxycarbonylamino)-1,2,3,4-tetrahydronaphthalen-7-yl]acrylate (252 mg) was dissolved in ethanol (10 ml), and 10% palladium on activated carbon (30 mg) was added to the solution, then the resulting mixture was stirred for 3 hours at room temperature under a hydrogen atmosphere. The reaction mixture was filtrated to remove the catalyst, and the filtrate was concentrated in vacuo. Recrystallization of the residue from diisopropyl ether gave ethyl (S)-3-[2-(tert-butoxycarbonylamino)-1,2,3,4-tetrahydronaphthalen-7-yl]propionate (236 mg) having a melting point of 101-102° C.

Workup

  1. filtrationThe reaction mixture was filtrated
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated in vacuo
  4. customRecrystallization of the residue from diisopropyl ether

Sources & evidence

ORD record
ord-ad8eb74a1fc441049743cdce49988132
Source dataset
uspto-grants-2000_10
Patent number
US06136852

Reaction notes

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