Diisopropylethylamine → Tert-butyl 5-hydroxy-2-methylpiperidine-1-carboxylate

HRID 1867384Notes

Reaction equation

HRID 1867384 reaction equation
Cl.O[CH2:3][C:4]1[N:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.CCN(C(C)C)C(C)C.[O:20](C(OC(C)(C)C)=O)[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=O>CN(C=O)C>[C:24]([O:23][C:21]([N:9]1[CH2:8][CH:7]([OH:10])[CH2:6][CH2:5][CH:4]1[CH3:3])=[O:20])([CH3:27])([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 90495Di-tert-butyl dicarbonateHCID 187584236-(Hydroxymethyl)pyridin-3-ol hydrochloride

Product 1

HCID 68434339Tert-butyl 5-hydroxy-2-methylpiperidine-1-carboxylateYield 17.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.50 g (9.28 mmol) of 6-Hydroxymethyl-pyridin-3-ol hydrochlorid was hydrogenated under the conditions described in intermediate 63B. The crude product was dissolved in 5 ml DMF, 5.60 ml (32.00 mmol) of Hunig's base and 3.56 g (16.00 mmol) of BOC2O were added and the yellow solution was stirred 18 h at RT. Evaporation, extraction (AcOEt/water/brine) and chromatography (silica gel, AcOEt/MeOH) gave 0.35 g (15%) (rac)-5-hydroxy-2-methyl-piperidine-1-carboxylic acid tert-butyl ester; MS: 216.4 (MH+)

Workup

  1. customEvaporation, extraction (AcOEt/water/brine) and chromatography (silica gel, AcOEt/MeOH)

Sources & evidence

ORD record
ord-5b09d3acd74343e6b4b5f54c21050fdb
Source dataset
uspto-grants-2009_12
Patent number
US07632829B2

Reaction notes

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