Acetic Acid → HCID 67455802, compound

HRID 469725Notes

Reaction equation

HRID 469725 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].C(O)(=O)C.[O:13]1[CH2:18][CH2:17][CH:16]([CH:19]=O)[CH2:15][CH2:14]1.S([O-])([O-])(=O)=O.[Na+].[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C>ClCCCl>[O:13]1[CH2:18][CH2:17][CH:16]([CH2:19][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

7

Reactant 5

HCID 176Acetic AcidHCID 24436Sodium SulfateHCID 145742L-ProlineHCID 2724942TriacetoxyborohydrideHCID 9964078Tetrahydro-2H-pyran-4-carboxaldehyde

Product 1

HCID 67455802HCID 67455802, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of L-proline (1 g; 8.686 mmol) in 1,2-dichloroethane (10 mL)/acetic acid (1.98 mL; 33.007 mmol)) is added tetrahydro-pyran-4-carbaldehyde (0.991 g; 8.686 mmol) and sodium sulfate (˜10 equivalents). After 45 minutes of agitation on an orbital shaker, MP-triacetoxyborohydride resin (4.272 g; 10.423 mmol) is added. The mixture is agitated at room temperature overnight and filtered, washing resin with methylene chloride. The combined filtrate is washed with aqueous saturated sodium bicarbonate 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. Title compound is afforded by this method. ESI m/z 214 [M+H]+

Workup

  1. filtrationfiltered
  2. washwashing resin with methylene chloride
  3. washThe combined filtrate is washed with aqueous saturated sodium bicarbonate 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-d5c289ed6d0e4d67abfda889006fa6f4
Source dataset
uspto-grants-2014_01
Patent number
US08629157B2

Reaction notes

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