HCID 86690735, compound → HCID 86690736, compound

HRID 1473918Notes

Reaction equation

HRID 1473918 reaction equation
[OH:1][C:2]1[C:3]([CH2:21][OH:22])=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][CH:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:9][CH2:8]1>C1COCC1.O=[Mn]=O>[CH:21]([C:3]1[C:2]([OH:1])=[CH:20][CH:19]=[CH:18][C:4]=1[CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][CH:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:11][CH2:12]1)=[O:22]

Participants

4

Reactant 1

HCID 86690735HCID 86690735, compound

Product 1

HCID 86690736HCID 86690736, compoundYield 94.7%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To ethyl 1-(3-hydroxy-2-(hydroxymethyl)phenethyl)piperidine-4-carboxylate (85 mg, crude above) in THF (20.0 mL) was added MnO2 (500 mg, 5.75 mmol) at rt. The mixture was stirred at rt for 1 h, filtered, and concentrated to give ethyl 1-(2-formyl-3-hydroxyphenethyl)piperidine-4-carboxylate (80 mg, crude) as a pale brown solid, which was used for next step with purification. LRMS (M+H+) m/z 306.1.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-f2fb57b1bffa45d88c813f52f2663dc8
Source dataset
uspto-grants-2015_04
Patent number
US09018210B2

Reaction notes

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