Methanol → HCID 69515882, compound

HRID 458434Notes

Reaction equation

HRID 458434 reaction equation
[F:1][C:2]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:3]=1[CH2:4][C:5]1[CH:6]=[C:7]([C:18]2[N:19]=[CH:20][C:21]([C:24]([O:26]CC)=[O:25])=[N:22][CH:23]=2)[C:8]2[C:15](=[O:16])[N:14]3[C@@H:10]([CH2:11][CH2:12][CH2:13]3)[C:9]=2[N:17]=1.O.CO>C1COCC1>[F:1][C:2]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:3]=1[CH2:4][C:5]1[CH:6]=[C:7]([C:18]2[N:19]=[CH:20][C:21]([C:24]([OH:26])=[O:25])=[N:22][CH:23]=2)[C:8]2[C:15](=[O:16])[N:14]3[C@@H:10]([CH2:11][CH2:12][CH2:13]3)[C:9]=2[N:17]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 962WaterHCID 69516031HCID 69516031, compound

Product 1

HCID 69515882HCID 69515882, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 5-[(9aS)-2-(2,4-difluorobenzyl)-5-oxo-7,8,9,9a-tetrahydro-5H-pyrido[2,3-a]pyrrolizin-4-yl]-2-pyrazinecarboxylate (0.250 g, 0.555 mmol) was dissolved in THF (4 mL), H2O (1 mL) and MeOH (1 mL) and LiOH monohydrate (0.035 g, 0.832 mmol) was added. The reaction mixture was stirred at ambient temperature for 45 min and then acidified to pH 5. The organics were extracted with CH2Cl2 and then dried (Na2SO4), filtered and concentrated to a white solid (0.200 g, 0.473 mmol, 85% yield): 1H NMR (CD3OD, 400 MHz) δ 9.36 (s, 2H), 7.74 (s, 1H), 7.41–7.35 (m, 1H), 6.97–6.91 (m, 2H), 4.86–4.83 (m, 1H), 4.33 (s, 2H), 3.71–3.64 (m, 1H), 3.48–3.41 (m, 1H), 2.46–2.38 (m, 3H), 1.42–1.38 (m, 1H).

Workup

  1. extractionThe organics were extracted with CH2Cl2
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered

Sources & evidence

ORD record
ord-00dd1679cca64c399cf86e3f9ae29b48
Source dataset
uspto-grants-2007_03
Patent number
US07189851B2

Reaction notes

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