1,2-Dichloroethane → (S)-1-(Tetrahydro-pyran-4-yl)-pyrrolidine-2-carboxylic acid

反応式

[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].ClCCCl.[O:13]1[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1.[O-]S([O-])(=O)=O.[Na+].[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C>>[O:13]1[CH2:18][CH2:17][CH:16]([N:1]2[CH2:8][CH2:7][CH2:6][C@H:2]2[C:3]([OH:5])=[O:4])[CH2:15][CH2:14]1

参加物

反応物 5

HCID 111,2-Dichloroethane

HCID 24436Sodium Sulfate

HCID 121599Tetrahydro-4H-pyran-4-one

HCID 145742L-Proline

HCID 2724942Triacetoxyborohydride

生成物 1

HCID 51980116(S)-1-(Tetrahydro-pyran-4-yl)-pyrrolidine-2-carboxylic acid

実験手順

To L-proline (1.00 g; 8.69 mmol) in 1,2-dichloroethane (10 mL) acetic acid (1.98 mL; 33.0 mmol)) is added tetrahydro-pyran-4-one (0.87 g; 8.69 mmol) and Na2SO4 (˜10 equivalents). After 45 minutes of agitation on an orbital shaker, Mp-triacetoxyborohydride resin (4.27 g; 10.42 mmol) is added. The mixture is agitated at RT overnight and filtered and the resin washed with DCM. The combined filtrate is washed with aq. sat. NaHCO3 solution and brine, dried (Na2SO4), filtered and concentrated in vacuo. Excess acetic acid is removed by successive azeotropic distillation with toluene on the rotary evaporator to afford (S)-1-(tetrahydro-pyran-4-yl)pyrrolidine-2-carboxylic acid. ESI-MS: 200 [M+H]+