Carbon tetrabromide → tert-Butyl 2-(bromomethyl)piperidine-1-carboxylate

HRID 2403433Notes

Reaction equation

HRID 2403433 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11](CO)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:16](Br)(Br)(Br)[Br:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]1[CH2:16][Br:17])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

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

Product 1

HCID 20624355tert-Butyl 2-(bromomethyl)piperidine-1-carboxylateYield 49.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-hydroxymethyl-piperidine-1-carboxylic acid tert-butyl ester (2.0 g) in anhydrous tetrahydrofuran (50 ml) was added carbon tetrabromide (6.2 g) and triphenylphosphine (4.88 g). the reaction mixture was stirred at room temperature for 3 days. The reaction mixture was filtered through celite. The filtrate was taken up in ethyl acetate, washed with water then brine, dried (MgSO4) and the solvent removed in vacuo give a crude product. This was purified using flash chromatography which yielded Bromomethyl-piperidine-1-carboxylic acid tert-butyl ester (1.287 g).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashed with water
  3. dry with materialbrine, dried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customgive a crude product
  6. customThis was purified

Sources & evidence

ORD record
ord-8d4dd3ddf3eb4e5cb2ef970d04b6c793
Source dataset
uspto-grants-2014_08
Patent number
US08802670B2

Reaction notes

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