Carbon tetrabromide → tert-Butyl 4-(bromomethyl)piperidine-1-carboxylate

HRID 1689916Notes

Reaction equation

HRID 1689916 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14]O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Br)(Br)(Br)[Br:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][Br:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 15512811tert-Butyl 4-(bromomethyl)piperidine-1-carboxylateYield 86.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Amine preparation: To a solution of 4-hydroxymethyl-piperidine-1-carboxylic acid tert-butyl ester (250 mg), in dry THF (15 mL), was added carbon tetrabromide (769 mg), and triphenyl phosphine (609 mg). The reaction mixture was stirred at room temperature for 24 h, and then the solvents were evaporated in vacuo to give a residue which was purified by flash chromatography to give 4-bromomethyl-piperidine-1-carboxylic acid tert-butyl ester (279 mg), as a colourless oil. To a solution of 4-bromomethyl-piperidine-1-carboxylic acid tent-butyl ester (240 mg), in dry DMF (5.0 mL), was added imidazole (129 mg). The reaction mixture was heated in a sealed reaction vial at 100° C. for 24 h, then cooled and the contents evaporated onto flash silica for purification. Treatment of this compound with HCl in DCM/MeOH yielded the desired amine, isolated as the hydrochloride salt.

Workup

  1. customthe solvents were evaporated in vacuo
  2. customto give a residue which
  3. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-78b436bf53d04b1291706085e094e208
Source dataset
uspto-grants-2012_04
Patent number
US08153629B2

Reaction notes

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