Acetic Acid → HCID 68312525, compound

HRID 1472912Notes

Reaction equation

HRID 1472912 reaction equation
[C:1]1([C:7]2[N:12]=[C:11]([CH:13]=O)[CH:10]=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:15][C@@H:16]([CH2:20][OH:21])[CH:17]([CH3:19])[CH3:18].C(O)(=O)C.C([BH3-])#N>CO>[CH3:18][CH:17]([CH3:19])[C@@H:16]([NH:15][CH2:13][C:11]1[CH:10]=[CH:9][CH:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:12]=1)[CH2:20][OH:21]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 498716Cyano-borohydrideHCID 6950587D-ValinolHCID 135224166-Phenylpyridine-2-carbaldehyde

Product 1

HCID 68312525HCID 68312525, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-phenylpicolinaldehyde (Tetrahedron Lett. 2010, 51, 5621-5623; 0.391 g, 2.133 mmol) in methanol (4 mL) at ambient temperature was added D-valinol (0.22 mL, 1.9 mmol) followed by acetic acid (0.4 mL, 8 mmol). After 5 min, MP-cyanoborohydride (2.5 mmol/g, 500 mg) was added and stirring continued overnight. The mixture was filtered and the filtrate partitioned between 1N NaOH and CH2Cl2. The organic phase extracted with 1N aqueous HCl. The organic layer was discarded and the aqueous phase was made basic with 1N NaOH and extracted with EtOAc. The organic extract dried, filtered and concentrated to provide 300 mg (57%) of the title compound. MS (DCI30 ) m/z 271 (M+H); 1H NMR (300 MHz, CDCl3) δ 8.04-7.93 (m, 2H), 7.73 (t, J=7.7 Hz, 1H), 7.62 (d, J=7.6 Hz, 1H), 7.53-7.35 (m, 3H), 7.21 (d, J=7.5 Hz, 1H), 4.06 (s, 2H), 3.72 (dd, J=11.0, 4.0 Hz, 1H), 3.52 (dd, J=11.0, 6.9 Hz, 1H), 2.55 (td, J=6.7, 4.0 Hz, 1H), 1.91 (td, J=13.6, 6.8 Hz, 1H), 1.05 (d, J=6.4 Hz, 3H), 0.96 (d, J=6.8 Hz, 3H).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate partitioned between 1N NaOH and CH2Cl2
  3. extractionThe organic phase extracted with 1N aqueous HCl
  4. extractionextracted with EtOAc
  5. extractionThe organic extract
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-448c918c82154780b5cbbe357cc63a58
Source dataset
uspto-grants-2015_04
Patent number
US09012651B2

Reaction notes

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