Toluene → 4-Hydroxy-piperidine-1-carboxylic acid tert-butyl ester chloroformate

HRID 39290

Reaction equation

HRID 39290 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)([Cl:17])=O.C1(C)C=CC=CC=1>C1COCC1>[Cl:17][C:6]([OH:5])=[O:7].[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6371PhosgeneHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 866555934-Hydroxy-piperidine-1-carboxylic acid tert-butyl ester chloroformate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (201 mg, 1.0 mmol) in THF (2 mL) was added a 20% solution of phosgene in toluene (358 μL, 1.7 mmol). The reaction was stirred at room temperature for 1 hour. The reaction was concentrated under reduced pressure.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b8798188cd69492386d462f7445ecae2
Source dataset
uspto-grants-2013_09
Patent number
US08524764B2

Linked notes

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