Water → HCID 59511142, compound

HRID 1157142Notes

Reaction equation

HRID 1157142 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][N:6]1[C:11]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][N:14]=1)=[O:12])=[O:4].O.[OH-].[Li+]>C1COCC1>[C:13]1([C:11]([N:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C@H:5]2[C:3]([OH:4])=[O:2])=[O:12])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][N:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 59511138HCID 59511138, compound

Product 1

HCID 59511142HCID 59511142, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of (S)-1-(isoquinoline-1-carbonyl)-2-piperidinecarboxylic acid methyl ester (1.05 g, 3.52 mmol) in THF (20 ml) at room temperature was treated with water (10 ml). Lithium hydroxide (84 mg, 3.51 mmol) was then added and the resulting mixture was stirred at room temperature for 16 hrs. The resulting mixture was concentrated to remove the organic solvent. The resulting solution was then washed with diethyl ether and the remaining aqueous layer was made acid with 2 N HCl. The resulting solution was extracted with ethyl acetate and the organic layer was separated, dried (Na2SO4), filtered and concentrated to reveal a white solid (902 mg, 90%): 1H NMR (400 MHz, d4-MeOH) δ 1.20-2.52 (6H, m), 3.10-3.39 (2H, m), 4.10-4.90 (1H, m), 7.68-8.55 (5H, m).

Workup

  1. concentrationThe resulting mixture was concentrated
  2. customto remove the organic solvent
  3. washThe resulting solution was then washed with diethyl ether
  4. extractionThe resulting solution was extracted with ethyl acetate
  5. customthe organic layer was separated
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e52c419e5ba44cd98b8e3c3996fdf7be
Source dataset
uspto-grants-2010_10
Patent number
US07807659B2

Reaction notes

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