Benzyl 4-formylpiperidine-1-carboxylate → HCID 68313085, compound

HRID 1530369Notes

Reaction equation

HRID 1530369 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH:17]=[O:18])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19]([Mg]Br)[CH3:20]>C1COCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH:17]([OH:18])[CH2:19][CH3:20])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2776272Benzyl 4-formylpiperidine-1-carboxylateHCID 178418443HCID 178418443, compound

Product 1

HCID 68313085HCID 68313085, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-formylpiperidine-1-carboxylic acid benzyl ester (1.0 g, 4.04 mmol) in THF (15 mL) at 0° C. was added ethylmagnesium bromide (1.0M in THF, 8.1 mL, 8.08 mmol) and the mixture was stirred at 0° for 1 h. The reaction mixture was then quenched with water and extracted with EtOAc. The organic phase was washed with brine, dried (MgSO4) and then concentrated in vacuo. The resulting residue was purified by column chromatography (Si-PCC, gradient 0-100% EtOAc in hexane) affording 4-(1-Hydroxypropyl)piperidine-1-carboxylic acid benzyl ester (690 mg, 62%). 1H NMR (CDCl3, 400 MHz): δ 7.38-7.27 (5H, m), 5.13 (2H, bs), 4.25 (2H, s), 3.36-3.29 (1H, m), 2.83-2.66 (2H, m), 1.85-1.77 (1H, bd, J=13.16 Hz), 1.64-1.19 (7H, m), 0.97 (3H, t, J=7.41 Hz).

Workup

  1. customThe reaction mixture was then quenched with water
  2. extractionextracted with EtOAc
  3. washThe organic phase was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by column chromatography (Si-PCC, gradient 0-100% EtOAc in hexane)

Sources & evidence

ORD record
ord-ca05a02e4bbc48c9a05519f392182dee
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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