Hydrochloric Acid → HCID 71621776, compound

HRID 1473919Notes

Reaction equation

HRID 1473919 reaction equation
[CH:1]([C:3]1[C:21]([OH:22])=[CH:20][CH:19]=[CH:18][C:4]=1[CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][CH:10]([C:13]([O:15]CC)=[O:14])[CH2:9][CH2:8]1)=[O:2].[OH-].[Na+].Cl>C1COCC1>[CH:1]([C:3]1[C:21]([OH:22])=[CH:20][CH:19]=[CH:18][C:4]=1[CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][CH:10]([C:13]([OH:15])=[O:14])[CH2:11][CH2:12]1)=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86690736HCID 86690736, compound

Product 1

HCID 71621776HCID 71621776, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To ethyl 1-(2-formyl-3-hydroxyphenethyl)piperidine-4-carboxylate (80 mg, crude above) in THF (5.0 mL) was added NaOH (3 N, 1.0 mL). The mixture was stirred at rt for 2 h and acidified to pH 3-4 using HCl (2 N). The mixture was concentrated and purified on RP-HPLC (Gemini 21.2 mm×150 mm) using a mixture of CH3CN and water (0.1% HCOOH) as eluent to give 1-(2-formyl-3-hydroxyphenethyl)piperidine-4-carboxylic acid (40 mg, 29% for three steps) as a yellow solid. 1H NMR (400 MHz, DMSO) δ 10.26 (s, 1H), 8.65 (s, 2H), 6.91 (dd, J=8.7, 6.9 Hz, 1H), 6.16 (d, J=7.9 Hz, 1H), 5.76 (d, J=6.7 Hz, 1H), 3.01-2.89 (m, 4H), 2.50-2.36 (m, 2H), 2.03 (t, J=10.3 Hz, 2H), 1.92-1.76 (m, 3H), 1.69-1.49 (m, 2H). LRMS (M+H+) m/z 278.4. 1H NMR (400 MHz, DMSO-d6) δ 10.1 (s, 1H), 8.55 (s, 2H), 6.75 (dd, J=Hz, 1H), 6.05 (d, J=Hz, 1H), 5.6 (d, J=Hz, 1H), 2.7 (m, 4H), 2.3 (m, 2H), 1.85 (m, 2H), 1.7 (m, 3H), 1.5 (m, 2H).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified on RP-HPLC (Gemini 21.2 mm×150 mm)
  3. additiona mixture of CH3CN and water (0.1% HCOOH) as eluent

Sources & evidence

ORD record
ord-b0a624adf60e46b29fe20b00446cf82a
Source dataset
uspto-grants-2015_04
Patent number
US09018210B2

Reaction notes

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