Triphenylphosphine → [6-(2-{3-[1,1-bis(Methylethyl)-2-methyl-1-silapropoxy]phenoxy}ethyl)(2-pyridyl)]methylamine

HRID 985496Notes

Reaction equation

HRID 985496 reaction equation
[CH3:1][CH:2]([Si:4]([CH:16]([CH3:18])[CH3:17])([O:8][C:9]1[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=1)[CH:5]([CH3:7])[CH3:6])[CH3:3].CN[C:21]1[N:26]=[C:25]([CH2:27][CH2:28]O)[CH:24]=[CH:23][CH:22]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:49]([C:56](OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:7][CH:5]([Si:4]([CH:16]([CH3:18])[CH3:17])([O:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=1)[O:15][CH2:28][CH2:27][C:25]1[N:26]=[C:21]([CH2:56][NH2:49])[CH:22]=[CH:23][CH:24]=1)[CH:2]([CH3:1])[CH3:3])[CH3:6]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 105348582-[6-(Methylamino)-2-pyridyl]ethan-1-olHCID 225070633-[1,1-bis(Methylethyl)-2-methyl-1-silapropoxy]phenol

Product 1

HCID 22507072[6-(2-{3-[1,1-bis(Methylethyl)-2-methyl-1-silapropoxy]phenoxy}ethyl)(2-pyridyl)]methylamineYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 3-[1,1-bis(methylethyl)-2-methyl-1-silapropoxy]phenol (200 mg,0.75 mmol),2-[6-(methylamino)-2-pyridyl]ethan-1-ol (104 mg, 0.68 mmol), triphenylphosphine (199 mg, 0.75 mmol) and THF (25 ml), was added diethyl azodicarboxylate (0.12 ml, 0.75 mmol) at 0° C. The reaction was stirred overnight under argon. The solvent was removed under vaccum and the crude product was chromatographed over silica gel to yield 76 mg (28%) of [6-(2-{3-[1,1-bis(Methylethyl)-2-methyl-1-silapropoxy]phenoxy}ethyl)(2-pyridyl)]methylamine. NMR 1H Cl3CD δ: 7.39 (m, 1H), 7.07 (t, 1H, J=8.0 Hz), 6.5 (m, 3H), 6.25 (d, 1H, J=8 Hz), 4.27 (t, 2H, J=6.8 Hz), 3.06 (t, 2H, J=6.8 Hz), 2.90 (d, 3H, J=8 Hz), 1.28 (m, 3H), 1.10 (d, 18H, J=7.0 Hz).

Workup

  1. customThe solvent was removed under vaccum
  2. customthe crude product was chromatographed over silica gel

Sources & evidence

ORD record
ord-7b4ae92f1ce7441282e69fd370277d1e
Source dataset
uspto-grants-2005_03
Patent number
US06872730B2

Reaction notes

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