Carbon tetrabromide → tert-Butyl 4-bromopiperidine-1-carboxylate

HRID 1900705Notes

Reaction equation

HRID 1900705 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11](O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:35]>C1COCC1>[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([Br:35])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 15541517tert-Butyl 4-bromopiperidine-1-carboxylateYield 89.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To N-Boc-4-hydroxy piperidine (20 g, 100 mmol) in THF (200 ml) at 0° C. was added triphenylphosphine (28.85 g, 110 mmol) followed by carbon tetrabromide (36.48 g, 110 mmol). The solution was stirred at room temperature for 2 h then filtered and concentrated under vacuum. Flash column chromatography using dichloromethane in hexane (10-70%) yielded the product as a colourless oil (23.6 g); δH (CDCl3) 1.47 (9H, s, t-Bu), 1.93 and 2.04 (4H, m, 3,5-piperidinyl CH2), 3.31 and 3.66 (4H, m, 2,6-piperidinyl CH2), and 4.39 (1H, m, 4-piperidinyl H).

Workup

  1. filtrationthen filtered
  2. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-727b75987321459f85bef0eefc78b4e5
Source dataset
uspto-grants-1996_11
Patent number
US05576336

Reaction notes

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