trans-[2-(Acryloyl-but-3-enyl-amino)-cyclohexyl]-carbamic acid tert-butyl ester → trans-[2-(6-Oxo-3,6-dihydro-2H-pyridin-1-yl)-cyclohexyl]-carbamic acid tert-butyl ester

HRID 2218564Notes

Reaction equation

HRID 2218564 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[N:14]([C:19](=[O:22])[CH:20]=[CH2:21])[CH2:15][CH2:16]C=C)([CH3:4])([CH3:3])[CH3:2]>ClCCl.C1CCC([P+](C([P+](C2CCCCC2)(C2CCCCC2)C2CCCCC2)C2C=CC=CC=2)(C2CCCCC2)C2CCCCC2)CC1.Cl[Ru]Cl.CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4]>[C:1]([O:5][C:6](=[O:23])[NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[N:14]1[C:19](=[O:22])[CH:20]=[CH:21][CH2:16][CH2:15]1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 1

HCID 68977079trans-[2-(Acryloyl-but-3-enyl-amino)-cyclohexyl]-carbamic acid tert-butyl ester

Product 1

HCID 68977820trans-[2-(6-Oxo-3,6-dihydro-2H-pyridin-1-yl)-cyclohexyl]-carbamic acid tert-butyl esterYield 96%

Reagents, catalysts & solvents 3

HCID 11026Titanium isopropoxideCatalystHCID 86306055bis(tricyclohexylphosphine)benzylidene ruthenium(IV) dichlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

Bis(tricyclohexylphosphine)benzylidene ruthenium(IV)dichloride (13 mg, 16 μmol) was added to a solution of trans-[2-(acryloyl-but-3-enyl-amino) -cyclohexyl]-carbamic acid tert-butyl ester (50 mg, 0.16 mmol) and tetraisopropyl orthotitanate (8.8 mg, 31 μmol) in dichloromethane (2.5 ml), and the reaction mixture was stirred for 1 h at room temperature. The solvent was then evaporated and the residue chromatographed (SiO2, heptane-ethyl acetate gradient) to produce the title compound (44 mg, 96%). Off-white solid, MS (ISP) 295.2 (M+H)+.

Workup

  1. customThe solvent was then evaporated
  2. customthe residue chromatographed (SiO2, heptane-ethyl acetate gradient)

Sources & evidence

ORD record
ord-6a5d59b0b3e24c43873bb787cc647806
Source dataset
uspto-grants-2008_08
Patent number
US07411093B2

Reaction notes

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