tert-Butyl 4-formylpiperidine-1-carboxylate → tert-Butyl 4-(1-hydroxyethyl)piperidine-1-carboxylate

HRID 1806088Notes

Reaction equation

HRID 1806088 reaction equation
[CH:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)=[O:2].[CH3:16][Mg]Br>C1COCC1>[OH:2][CH:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)[CH3:16]

Participants

4

Reactant 2

HCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 178418573HCID 178418573, compound

Product 1

HCID 21989903tert-Butyl 4-(1-hydroxyethyl)piperidine-1-carboxylateYield 90.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Placed tert-butyl 4-formylpiperidine-1-carboxylate (2.00 g, 9.38 mmol) in THF (40 mL) and cooled to −78° C. Slowly added methylmagnesium bromide (3.44 mL, 10.3 mmol) stirred for 1 hour. Slowly added saturated ammonium chloride and extracted with CH2Cl2. Concentrated and redissolved in 5% MeOH in CH2Cl2. Added ether and filtered off solids. Concentrate filtrate to give the title compound (1.94 g, 90.2% yield)

Workup

  1. extractionSlowly added saturated ammonium chloride and extracted with CH2Cl2
  2. concentrationConcentrated
  3. dissolutionredissolved in 5% MeOH in CH2Cl2
  4. filtrationAdded ether and filtered off solids

Sources & evidence

ORD record
ord-8fb53056965f44d7b45a828b40d7e72b
Source dataset
uspto-grants-2013_01
Patent number
US08354540B2

Reaction notes

Loading…