tert-Butyl 3-(hydroxymethyl)piperidine-1-carboxylate → 1-Boc-piperidine-3-carboxaldehyde

HRID 1521929Notes

Reaction equation

HRID 1521929 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[CH:2]([CH:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1)=[O:1]

Participants

4

Reactant 2

HCID 2763851tert-Butyl 3-(hydroxymethyl)piperidine-1-carboxylateHCID 178418287HCID 178418287, compound

Product 1

HCID 99644481-Boc-piperidine-3-carboxaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 1B (5 g, 23.22 mmol) in dichloromethane (50 mL) was added pyridinium chlorochromate (10.01 g, 46.4 mmol) and the mixture was stirred for 12 hours. The mixture was filtered and concentrated to afford crude product which was purified by column chromatography (silica gel, 40% ethyl acetate in hexane) to afford the title compound. 1H NMR (300 MHz, CDCl3): δ 1.44 (s, 9H), 1.5-1.54 (m, 1H), 1.66-1.69 (m, 2H), 1.9-2.0 (m, 1H), 2.38-2.46 (m, 1H), 3.04-3.12 (m, 1H), 2.38-3.36 (m, 1H), 3.6-3.68 (m, 1H), 3.88-4.0 (m, 1H), 9.7 (s, 1H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. customto afford crude product which
  4. customwas purified by column chromatography (silica gel, 40% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-ac7f7f63ed444d0b937977f70de2d183
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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