N-[1-((1R,2S)-2-Dibenzylamino-1-hydroxy-3-phenyl-propyl)-pent-4-enyl]-acrylamide → 7-((1R,2S)-2-dibenzylamino-1-hydroxy-3-phenylpropyl)-1,5,6,7-tetrahydroazepin-2-one

HRID 1436732Notes

Reaction equation

HRID 1436732 reaction equation
[CH2:1]([N:8]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C@@H:9]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C@@H:10]([CH:12]([NH:17][C:18](=[O:21])C=C)[CH2:13][CH2:14][CH:15]=[CH2:16])[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>ClCCl.CC1C=C(C)C(N2C(=[Ru](Cl)(Cl)=CC3C=CC=CC=3)N(C3C(C)=CC(C)=CC=3C)CC2)=C(C)C=1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1>[CH2:29]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C@@H:9]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C@@H:10]([CH:12]1[NH:17][C:18](=[O:21])[CH:16]=[CH:15][CH2:14][CH2:13]1)[OH:11])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

4

Reactant 1

HCID 69016262N-[1-((1R,2S)-2-Dibenzylamino-1-hydroxy-3-phenyl-propyl)-pent-4-enyl]-acrylamide

Product 1

HCID 690155047-((1R,2S)-2-dibenzylamino-1-hydroxy-3-phenylpropyl)-1,5,6,7-tetrahydroazepin-2-one

Reagents, catalysts & solvents 2

HCID 11147261(1,3-Dimesitylimidazolidin-2-ylidene)(tricyclohexylphosphine)benzylidene ruthenium dichlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

Dissolve N-[1-((1R,2S)-2-dibenzylamino-1-hydroxy-3-phenyl-propyl)-pent-4-enyl]-acrylamide (0.5 g, 1.06 mmol) in dichloromethane (50 mL) under nitrogen atmosphere and add Grubb's second generation catalyst (20% mol). Stir the reaction at 50° C. for one day. Concentrate under reduced pressure. Purify on silica gel with hexane/ethyl acetate mixtures to give a mixture of two products. (0, 210 g, 45%) that may be separated using HPLC-MS (19×300 mm, 7 μm, C-18 column; flow rate=20 mL/min; mobile phase gradient 5%-95% over 26 minutes; Solvent A: acetonitrile; Solvent B: 0.1% trifluoroacetic acid in water).

Workup

  1. customthe reaction at 50° C. for one day
  2. concentrationConcentrate under reduced pressure
  3. customPurify on silica gel with hexane/ethyl acetate
  4. customto give
  5. additiona mixture of two products
  6. custom(0, 210 g, 45%) that may be separated
  7. customHPLC-MS (19×300 mm, 7 μm, C-18 column; flow rate=20 mL/min; mobile phase gradient 5%-95% over 26 minutes; Solvent A: acetonitrile; Solvent B: 0.1% trifluoroacetic acid in water)

Sources & evidence

ORD record
ord-cdc3b43744a84521abd2c89bc11eb03b
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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