Lithium hydroxide, monohydrate → HCID 68710012, compound

HRID 222116Notes

Reaction equation

HRID 222116 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][N:10]1[C:14]2[C:15]3[CH:16]=[CH:17][N:18]=[CH:19][C:20]=3[CH2:21][CH2:22][C:13]=2[C:12]([C:23]([O:25]C)=[O:24])=[CH:11]1.C1COCC1.CO.O.O.[OH-].[Li+]>C(OCC)C>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][N:10]1[C:14]2[C:15]3[CH:16]=[CH:17][N:18]=[CH:19][C:20]=3[CH2:21][CH2:22][C:13]=2[C:12]([C:23]([OH:25])=[O:24])=[CH:11]1

Participants

5

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 21892291Methanol tetrahydrofuran waterHCID 68709906HCID 68709906, compound

Product 1

HCID 68710012HCID 68710012, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of methyl 1-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-4,5-dihydro-1H-pyrrolo[2,3-f]isoquinoline-3-carboxylate E17 (1.4 mmol) in 30 mL of a mixture THF/MeOH/H2O 8:1:1, lithium hydroxide monohydrate (2.8 mmol) was added. The resulting solution was stirred at reflux for 6 h. The solvent was removed, the residue redissolved in water and neutralized with aq KH2PO4. The desired product was extracted with DCM/methanol 9:1 and the organic layer was dried (Na2SO4) and evaporated to give, after trituration with diethylether, the title compound (63% yield). ESI (+) MS: m/z 343 (MH+); MS (ES−) 341. 1H NMR: 1.30-1.55 (m, 6H), 2.79-2.86 (m, 2H), 2.87-2.97 (m, 2H), 3.31-3.51 (m, 2H), 3.68-3.75 (m, 1H), 3.86-3.94 (m, 1H), 4.49-4.57 (m, 3H), 7.63-7.67 (m, 1H), 7.68 (s, 1H), 8.44 (d, J=5.61, 1H), 8.47 (s, 1H), 12.06 (bs, 1H).

Workup

  1. temperatureat reflux for 6 h
  2. customThe solvent was removed
  3. dissolutionthe residue redissolved in water and neutralized with aq KH2PO4
  4. extractionThe desired product was extracted with DCM/methanol 9:1
  5. dry with materialthe organic layer was dried (Na2SO4)
  6. customevaporated
  7. customto give

Sources & evidence

ORD record
ord-20575c5b0ccc4581837798ed2788fde0
Source dataset
uspto-grants-2012_06
Patent number
US08207180B2

Reaction notes

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