Imidazole → HCID 21180602, compound

HRID 1386758Notes

Reaction equation

HRID 1386758 reaction equation
OCC[CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.N1[CH:21]=[CH:20]N=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:41]I>CCOCC.CCOCC.CC#N>[C:13]([O:12][C:10]([N:7]1[CH2:6][CH2:5][CH2:4][CH2:9][CH:8]1[CH2:20][CH2:21][I:41])=[O:11])([CH3:14])([CH3:15])[CH3:16]

Participants

7

Reactant 4

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

Product 1

HCID 21180602HCID 21180602, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21885917Acetonitrile etherSolvent

Procedure

A solution of 4-(2-hydroxyethyl)-1-(t-butoxycarbonyl)-piperidine (4.5 g, 19.6 mmol, from EXAMPLE 113, Step A), imidazole (1.8 g, 27 mmol) and triphenylphosphine (7.1 g, 27 mmol) in 60 mL of 2:1 v/v ether/CH3CN at 0° C. was treated with 7.4 g (29 mmol) of iodine. The mixture was warmed to rt and stirred for 15 min. The mixture was diluted with 200 mL of ether and washed with sat'd Na2SO4 (2×200 mL), sat'd CaSO4 (100 mL) and sat'd NaCl. The organic phase was dried over Na2SO4 and concentrated. The material was filtered through a pad of silica to remove the triphenylphosphine oxide providing 6.1 g (92%) of the title compound: 1H NMR (300 MHz) δ 1.0-1.2 (m, 2H), 1.45 (s, 9H), 1.55 (m, 1H), 1.7-1.8 (m, 4H), 2.6-2.8 (m, 2H), 3.19-3.25 (t, 2H), 4.04.2 (m, 2H).

Workup

  1. washwashed with sat'd Na2SO4 (2×200 mL), sat'd CaSO4 (100 mL)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated
  4. filtrationThe material was filtered through a pad of silica
  5. customto remove the triphenylphosphine oxide providing 6.1 g (92%) of the title compound

Sources & evidence

ORD record
ord-66d41b0d16b34639a7389e7b56552157
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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