Water → HCID 86681848, compound

HRID 2276547Notes

Reaction equation

HRID 2276547 reaction equation
[C:1]([O:4][C@@H:5]1[C:14]2[C:9](=[N:10][C:11]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:13]=2)[NH:8][CH2:7][CH2:6]1)(=[O:3])[CH3:2].O=[CH:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>ClCCCl.CO>[C:1]([O:4][C@@H:5]1[C:14]2[C:9](=[N:10][C:11]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:13]=2)[N:8]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH2:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 77609Heptanoic acid, 7-oxo-, ethyl ester2×HCID 5049666Sodium triacetoxyborohydrideHCID 66665758HCID 66665758, compound

Product 1

HCID 86681848HCID 86681848, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolvent

Procedure

To a solution of (S)-2,3-diphenyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazin-8-yl acetate (Intermediate HBS) (46 mg, 0.133 mmol) in DCE (7 ml) was added ethyl 7-oxoheptanoate (68.8 mg, 0.4 mmol) followed by sodium triacetoxyborohydride (226 mg, 1.065 mmol). The reaction mixture was left to stir at room temperature overnight under an atmosphere of nitrogen. A further portion of ethyl 7-oxoheptanoate (71.8 mg, 0.417 mmol) was added. The reaction mixture was left to stir for a further 5 hours under an atmosphere of nitrogen. Water (20 ml) was added and the resulting mixture was extracted with EtOAc (3×20 ml). The combined organic extracts were dried over MgSO4, filtered and concentrated to give a crude oil. The resulting crude product was purified by chromatography on silica eluting with 0-40% EtOAc/iso-hexane to afford an oil. The compound was passed through a pre-conditioned Isolute SCX-2 SPE column loading with MeOH and eluting with 1M ammonia in MeOH (20 ml) to afford the title compound;

Workup

  1. waitThe reaction mixture was left
  2. waitThe reaction mixture was left
  3. stirringto stir for a further 5 hours under an atmosphere of nitrogen
  4. extractionthe resulting mixture was extracted with EtOAc (3×20 ml)
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a crude oil
  9. customThe resulting crude product was purified by chromatography on silica eluting with 0-40% EtOAc/iso-hexane
  10. customto afford an oil
  11. washeluting with 1M ammonia in MeOH (20 ml)

Sources & evidence

ORD record
ord-a4fddd002fd64086b854d36c92e049fe
Source dataset
uspto-grants-2015_09
Patent number
US09132127B2

Reaction notes

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