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

HRID 1789788Notes

Reaction equation

HRID 1789788 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].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:36]>C(OCC)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][Br:36])[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 73.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution 4-hydroxymethyl-piperidine-1-carboxylic acid tert-butyl ester (8.75 g, 40.64 mmol) in diethyl ether (200 mL) at 0° C. under nitrogen. were added triphenyl phosphine (21.32 g, 81.28 mmol) and carbon tetrabromide (26.96 g, 81.28 mmol). The mixture was allowed to warm to room temperature and stirred under nitrogen for 48 h. The reaction mixture was filtered through a pad of Celite and the organic filtrate was washed with 5% NaS2O3, water, brine, and dried. The mixture was filtered and concentrated under reduced pressure. The crude product was purified by column chromatography (ethyl acetate/hexane, 1:9) to give 4-bromomethyl-piperidine-1-carboxylic acid tert-butyl ester (8.26 g, 73%).

Workup

  1. customat 0° C.
  2. filtrationThe reaction mixture was filtered through a pad of Celite
  3. washthe organic filtrate was washed with 5% NaS2O3, water, brine
  4. customdried
  5. filtrationThe mixture was filtered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography (ethyl acetate/hexane, 1:9)

Sources & evidence

ORD record
ord-0c62e6cebadc470dbabcf15e2d3a6fe2
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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