Water → HCID 66846924, compound

HRID 254162Notes

Reaction equation

HRID 254162 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][O:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:6]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[C:26]1([C:13]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[O:12][CH2:11][C:7]2[N:6]=[C:5]([CH2:4][NH2:1])[CH:10]=[CH:9][CH:8]=2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 86066890HCID 86066890, compound

Product 1

HCID 66846924HCID 66846924, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(azidomethyl)-6-(triphenylmethoxymethyl)pyridine (2.78 g, 6.8 mmol) in THF (25 mL) was treated with triphenylphosphine (1.96 g, 7.5 mmol), stirred at room temperature for 3 h, treated with water (184 μl, 10.2 mmol), stirred at room temperature for a further 7 days and concentrated in vacuo. The resulting oil was purified by chromatography [SiO2; EtOAc:MeOH:NH3 (1:0:0) to (9:1:0.2)] to give the title compound (2.33 g, 90%) as a yellow oil; NMR δH (400 MHz, CDCl3) 1.74 (2H, s), 3.90 (2H, s), 4.34 (2H, s), 7.14-7.33 (10H, m), 7.50-7.52 (6H, m) and 7.65-7.74 (2H, m); M/Z 381 (M+H)+

Workup

  1. stirringstirred at room temperature for a further 7 days
  2. concentrationconcentrated in vacuo
  3. customThe resulting oil was purified by chromatography [SiO2; EtOAc:MeOH:NH3 (1:0:0) to (9:1:0.2)]

Sources & evidence

ORD record
ord-43d01d051d6541bf875dc02b2021cc33
Source dataset
uspto-grants-2011_01
Patent number
US07875600B2

Reaction notes

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