(S)-tert-butyl 4-((R)-2-(allyloxymethyl)pent-4-enyl)-2,2-dimethyloxazolidine-3-carboxylate → (S)-tert-butyl 2,2-dimethyl-4-(((R,Z)-2,3,4,7-tetrahydrooxepin-3-yl)methyl)oxazolidine-3-carboxylate

HRID 451828Notes

Reaction equation

HRID 451828 reaction equation
[CH2:1]([O:4][CH2:5][C@H:6]([CH2:22][CH:23]=[CH2:24])[CH2:7][C@H:8]1[CH2:12][O:11][C:10]([CH3:14])([CH3:13])[N:9]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])C=C>C(Cl)Cl.Cl[Ru](=C1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)(Cl)(=CC1C=CC=CC=1)[P](C1CCCCC1)(C1CCCCC1)C1CCCCC1>[CH3:14][C:10]1([CH3:13])[N:9]([C:15]([O:17][C:18]([CH3:21])([CH3:19])[CH3:20])=[O:16])[C@@H:8]([CH2:7][C@H:6]2[CH2:22][CH:23]=[CH:24][CH2:1][O:4][CH2:5]2)[CH2:12][O:11]1

Participants

4

Reactant 1

HCID 59201545(S)-tert-butyl 4-((R)-2-(allyloxymethyl)pent-4-enyl)-2,2-dimethyloxazolidine-3-carboxylate

Product 1

HCID 59201476(S)-tert-butyl 2,2-dimethyl-4-(((R,Z)-2,3,4,7-tetrahydrooxepin-3-yl)methyl)oxazolidine-3-carboxylateYield 88%

Reagents, catalysts & solvents 2

HCID 178425456HCID 178425456, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl 4-((R)-2-(allyloxymethyl)pent-4-enyl)-2,2-dimethyloxazolidine-3-carboxylate (700 mg, 2.06 mmol, 1 eq) in anhydrous CH2Cl2 was added Grubbs catalyst 2nd generation ((1,3-Bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene)dichloro(phenylmethylene)(tricyclohexylphosphine)ruthenium) (173 mg, 0.21 mol, 0.1 eq). The resulting mixture was stirred and heated to reflux for 4 h. The solvent was removed under reduced pressure to afford the crude product. It was purified by column chromatography on silica gel (PE:EA=100:1) to give (S)-tert-butyl 2,2-dimethyl-4-(((R,Z)-2,3,4,7-tetrahydrooxepin-3-yl)methyl)oxazolidine-3-carboxylate (563 mg, 88%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 h
  3. customThe solvent was removed under reduced pressure
  4. customto afford the crude product
  5. customIt was purified by column chromatography on silica gel (PE:EA=100:1)

Sources & evidence

ORD record
ord-a33e1d280b474af88d0da83e2bf37a6a
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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