Imidazole → Tert-butyl 4-(2-iodoethyl)piperidine-1-carboxylate

HRID 419411Notes

Reaction equation

HRID 419411 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15]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.N1C=CN=C1.[I:41]I>C1COCC1>[I:41][CH2:15][CH2:14][CH:11]1[CH2:12][CH2:13][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 8541401-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidine

Product 1

HCID 9974426Tert-butyl 4-(2-iodoethyl)piperidine-1-carboxylateYield 85.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To N-Boc-4-piperidine-ethanol (5.00 g, 21.8 mmol) in THF (100 mL) was added triphenylphosphine (6.29 g, 24.0 mmol), imidazole (1.64 g, 24.1 mmol) and iodine (6.09 g, 24.0 mmol). The reaction was stirred at rt for 2 h. The mixture was filtered through Celite® purified by flash chromatography to provide the title compound of step A (6.31 g, 18.6 mmol, 85%). 1H NMR (400 MHz, CDCl3) δ ppm 1.07 (dq, J=12.2, 4.3 Hz, 2H), 1.42 (s, 9H), 1.49-1.58 (m, 1H), 1.62 (d, J=13.2 Hz, 2H), 1.75 (q, J=7.1 Hz, 2H), 2.67 (td, J=12.9, 2.5 Hz, 2H), 3.18 (t, J=7.1 Hz, 2H), 4.06 (d, J=13.0 Hz, 2H).

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-41d6164d6c1a4652868a580efc7cbee5
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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