methyl (E)-2-(tert-butoxycarbonylamino)-3-tetrahydropyran-4-yl-prop-2-enoate → methyl N-(tert-butoxycarbonyl)-3-(tetrahydro-2H-pyran-4-yl)-L-alaninate

HRID 1972339Notes

Reaction equation

HRID 1972339 reaction equation
[C:1]([O:5][C:6]([NH:8]/[C:9](=[CH:14]/[CH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)/[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:10]([O:12][CH3:13])=[O:11])[CH2:14][CH:15]1[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 66582522methyl (E)-2-(tert-butoxycarbonylamino)-3-tetrahydropyran-4-yl-prop-2-enoateHCID 178418361HCID 178418361, compound

Product 1

HCID 29947234methyl N-(tert-butoxycarbonyl)-3-(tetrahydro-2H-pyran-4-yl)-L-alaninate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 250-mL pressure tube was charged with methyl (2E)-2-((tert-butoxycarbonyl)amino)-3-(tetrahydro-2H-pyran-4-yl)-2-propenoate (8.75 g, 30.7 mmol), MeOH (100 mL), and rhodium[(1R,1′R,2R,2′R)-2,2′-bis(1,1-dimethylethyl)-2,2′,3,3′-tetrahydro-1,1′-bi-1H-isophosphindole-κP2,κP2′][(1,2,5,6-η)-1,5-cyclooctadiene]tetrafluoroborate (0.209 g, 0.30 mmol, ChiralQuest, Monmouth Junction, N.J.). The mixture was stirred under a 50 psi (344 kilopascal) hydrogen atmosphere for 3 h. The mixture was then filtered through a pad of silica, washing with 1:1 EtOAc in hexanes, and then concentrated to give methyl N-(tert-butoxycarbonyl)-3-(tetrahydro-2H-pyran-4-yl)-L-alaninate.

Workup

  1. filtrationThe mixture was then filtered through a pad of silica
  2. washwashing with 1:1 EtOAc in hexanes
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ceb779dde6944bf6a7d5c9a1e4a10feb
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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