Acetic Acid → HCID 86671315, compound

HRID 1472914Notes

Reaction equation

HRID 1472914 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH:8]=O)[CH:5]=[CH:4][CH:3]=1.[NH2:10][C@@H:11]([CH2:15][OH:16])[CH:12]([CH3:14])[CH3:13].C(O)(=O)C.C([BH3-])#N>CO>[Br:1][C:2]1[N:7]=[C:6]([CH2:8][NH:10][C@H:11]([CH:12]([CH3:14])[CH3:13])[CH2:15][OH:16])[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 498716Cyano-borohydrideHCID 27570096-Bromopyridine-2-carbaldehydeHCID 6950587D-Valinol

Product 1

HCID 86671315HCID 86671315, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-bromopyridine-2-carbaldehyde (5.00 g, 26.9 mmol) in methanol (75 mL) at ambient temperature was added D-valinol (3.00 mL, 26.9 mmol) followed by acetic acid (6.2 mL, 110 mmol). After 5 minutes, MP-cyanoborohydride (2.49 mmol/g; 12 g) was added and stirred overnight. The mixture was filtered, concentrated. The residue was partitioned between 1N NaOH and CH2Cl2. The organic phase was dried (Na2SO4) and concentrated. The residue was purified by chromatography (50% ethyl acetate:CH2Cl2 to remove non polar impurites, then ethyl acetate to 20% acetone:ethyl acetate) to provide 4.39 g (60%) of the title compound. MS (DCI30 ) m/z 273/275 (M+H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. customThe residue was partitioned between 1N NaOH and CH2Cl2
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (50% ethyl acetate
  7. customCH2Cl2 to remove non polar impurites

Sources & evidence

ORD record
ord-9c15b2fa62c147c4af4d8f8cab7b6387
Source dataset
uspto-grants-2015_04
Patent number
US09012651B2

Reaction notes

Loading…