Methanol → HCID 90050554, compound

HRID 931400Notes

Reaction equation

HRID 931400 reaction equation
O.[OH-].[Li+].[CH3:4][CH:5]1[C:13]2([C:21]3[C:16](=[N:17][CH:18]=[CH:19][CH:20]=3)[NH:15][C:14]2=[O:22])[CH2:12][C:11]2[C:6]1=[CH:7][CH:8]=[C:9]([C:23]([O-:25])=[O:24])[CH:10]=2.CO>C1COCC1>[CH3:4][CH:5]1[C:13]2([C:21]3[C:16](=[N:17][CH:18]=[CH:19][CH:20]=3)[NH:15][C:14]2=[O:22])[CH2:12][C:11]2[C:6]1=[CH:7][CH:8]=[C:9]([C:23]([OH:25])=[O:24])[CH:10]=2

Participants

5

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 131735168HCID 131735168, compound

Product 1

HCID 90050554HCID 90050554, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of lithium hydroxide monohydrate (31 mg, 0.73 mmol) and methyl (1R,2S and 1S,2R)-1-methyl-2′-oxo-1,1′,2′,3-tetrahydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridine]-5-carboxylate (75 mg, 0.24 mmol) in THF (5 mL) and methanol (5 mL) was stirred at 23° C. for 5 h, concentrated. The residue was acidified with saturated aqueous citric acid solution to pH 2, and extracted with ethyl acetate (2×). The combined organic layers were washed with water, brine, dried over anhydrous sodium sulfate, and concentrated to give the title compound as a racemic mixture. MS: m/z=295.2 (M+1); 1H NMR (400 MHz, DMSO-d6): δ 12.75 (br. s, 1H), 10.96 (s, 1H), 8.10 (d, 1H, J=3.9 Hz), 7.76-7.87 (m, 3H), 7.30 (d, 1H, J=7.9 Hz), 7.01 (dd, 1H, J=5.1, 7.3 Hz), 3.75 (q, 1H, J=7.0 Hz), 3.39 (d, 1H, J=16.1 Hz), 3.27 (d, 1H, J=16.1 Hz), 1.11 (d, 3H, J=7.0 Hz).

Workup

  1. concentrationconcentrated
  2. extractionextracted with ethyl acetate (2×)
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5e26a0f2393248179c5cfed31b770660
Source dataset
uspto-grants-2016_03
Patent number
US09296750B2

Reaction notes

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