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

HRID 538646Notes

Reaction equation

HRID 538646 reaction equation
[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

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 24436Sodium SulfateHCID 121599Tetrahydro-4H-pyran-4-oneHCID 145742L-ProlineHCID 2724942Triacetoxyborohydride

Product 1

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

Procedure

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]+

Workup

  1. filtrationfiltered
  2. washthe resin washed with DCM
  3. washThe combined filtrate is washed with aq. sat. NaHCO3 solution and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customExcess acetic acid is removed by successive azeotropic distillation with toluene on the rotary evaporator

Sources & evidence

ORD record
ord-2345d90dc80f4aa28efeaddb8d181caf
Source dataset
uspto-grants-2014_10
Patent number
US08865744B1

Reaction notes

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