Pyridine → Tert-butyl 4-(3-methoxyphenyl)-3-oxopiperidine-1-carboxylate

HRID 60372Notes

Reaction equation

HRID 60372 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)[CH:10]([OH:22])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)[C:10](=[O:22])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 159087TriacetoxyperiodinaneHCID 45074241HCID 45074241, compound

Product 1

HCID 54596007Tert-butyl 4-(3-methoxyphenyl)-3-oxopiperidine-1-carboxylateYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(±)-3-Hydroxy-4-(3-methoxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (1.27 g, 4.13 mmol) and pyridine (334 uL, 4 mmol) in methylene chloride (70 mL) at 0° C. were treated with Dess-Martin periodinane (3.5 g, 8.3 mmol) and then the reaction was stirred at room temperature for 2 h. The reaction was quenched by addition of a mixture of sat. solution of Na2S2O3 and sat. solution of NaHCO3 (1:1 v:v) (50 ml), which was followed by extraction with ether. The product was isolated by flash chromatography to afford (±)-4-(3-methoxy-phenyl)-3-oxo-piperidine-1-carboxylic acid tert-butyl ester (0.94 g, 75% yield). 1H NMR (CDCl3): δ ppm 7.27 (s, 1H), 6.83 (d, J=8.1 Hz, 1H), 6.70-6.75 (m, 1H), 6.68 (s, 1H), 4.24 (d, J=18.2 Hz, 1H), 4.06 (d, J=18.2 Hz, 2H), 3.80 (s, 3H), 3.62 (dd, J=11.5, 5.9 Hz, 1H), 3.51 (br. s., 1H), 2.19-2.35 (m, 2H), 1.44-1.53 (m, 9H).

Workup

  1. customThe reaction was quenched by addition of a mixture of sat. solution of Na2S2O3 and sat. solution of NaHCO3 (1:1 v:v) (50 ml), which
  2. extractionwas followed by extraction with ether
  3. customThe product was isolated by flash chromatography

Sources & evidence

ORD record
ord-658540d7305f4f1fa43687c99d06a603
Source dataset
uspto-grants-2016_09
Patent number
US09440984B2

Reaction notes

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