(S)-4-(2-allyloxy-pent-4-enyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid t-butyl ester → (S)-4-(3,6-dihydro-2H-pyran-2-ylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid t-butyl ester

HRID 19029Notes

Reaction equation

HRID 19029 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][CH:14]([O:18][CH2:19][CH:20]=[CH2:21])[CH2:15]C=C)[CH2:11][O:10][C:9]1([CH3:23])[CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]>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>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][CH:14]2[CH2:15][CH:21]=[CH:20][CH2:19][O:18]2)[CH2:11][O:10][C:9]1([CH3:22])[CH3:23])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 59344939(S)-4-(2-allyloxy-pent-4-enyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid t-butyl ester

Product 1

HCID 59344953(S)-4-(3,6-dihydro-2H-pyran-2-ylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid t-butyl esterYield 92%

Reagents, catalysts & solvents 2

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

Procedure

To a solution of (S)-4-(2-allyloxy-pent-4-enyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid t-butyl ester (1.38 g, 4.24 mmol) in dichloromethane (10 mL) was added benzylidene[1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro-(tricyclohexylphosphine)ruthenium (144 mg, 4% equivalent). The mixture was stirred at room temperature for 4 h. Solvents were evaporated and the residue was purified through flash column chromatography (silica gel, 0-20% ethyl acetate/hexanes) to afford (S)-4-(3,6-dihydro-2H-pyran-2-ylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid t-butyl ester (1.16 g, 92%) as a brown oil: 1H NMR (300 MHz, CDCl3) δ ppm 1.48 (s, 12H), 1.56, 16.0 (2×s, 3H), 1.69 (br. s., 1H), 1.81-2.20 (m, 3H), 3.55 (br. s., 1H), 3.83-4.02 (m, 2H), 4.00-4.28 (m, 3H), 5.61-5.93 (m, 2H).

Workup

  1. customSolvents were evaporated
  2. customthe residue was purified through flash column chromatography (silica gel, 0-20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-98802efe7a8944d78ee3cbe7eef87bce
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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