Triphenylphosphine → 3-((4-Cyclopentylphenoxy)methyl)pyridin-2-amine

HRID 2036004Notes

Reaction equation

HRID 2036004 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH2:34][C:35]1[C:40]([CH2:41][OH:42])=[CH:39][CH:38]=[CH:37][N:36]=1.[CH:43]1([C:48]2[CH:53]=[CH:52][C:51](O)=[CH:50][CH:49]=2)[CH2:47][CH2:46][CH2:45][CH2:44]1>C1COCC1>[CH:43]1([C:48]2[CH:49]=[CH:50][C:51]([O:42][CH2:41][C:40]3[C:35]([NH2:34])=[N:36][CH:37]=[CH:38][CH:39]=3)=[CH:52][CH:53]=2)[CH2:44][CH2:45][CH2:46][CH2:47]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 152024-CyclopentylphenolHCID 5363146Diisopropyl azodicarboxylateHCID 11159325(2-Aminopyridin-3-yl)methanol

Product 1

HCID 682809293-((4-Cyclopentylphenoxy)methyl)pyridin-2-amineYield 8.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropylazodicarboxylate (0.714 mL) was added to a solution of triphenylphosphine (951 mg), (2-aminopyridin-3-yl)methanol (300 mg) and 4-cyclopentylphenol (392 mg) in THF (dry) (20 mL) at room temperature and the mixture was stirred for 20 hr. Volatiles were removed in vacuo with silica-gel. The silica-supported mixture was purified by column chromatography (1st; NH-silica gel, eluted with EtOAc in hexane, 2nd; silica gel, eluted with EtOAc in hexane) to give the title compound (55.4 mg) as a white powder.

Workup

  1. customVolatiles were removed in vacuo with silica-gel
  2. customwas purified by column chromatography (1st; NH-silica gel, eluted with EtOAc in hexane, 2nd; silica gel, eluted with EtOAc in hexane)

Sources & evidence

ORD record
ord-f7ff855c9cd3434897a4fd7824bc0f8c
Source dataset
uspto-grants-2013_11
Patent number
US08575154B2

Reaction notes

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