Triphenylphosphine → [2-(4-Pyrazole-1-yl-phenoxy)-ethyl]-carbamic acid benzyl ester

HRID 413306Notes

Reaction equation

[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:33][CH2:34][NH:35][C:36](=[O:45])[O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1.C1(C)C=CC=CC=1>[CH2:38]([O:37][C:36](=[O:45])[NH:35][CH2:34][CH2:33][O:12][C:9]1[CH:10]=[CH:11][C:6]([N:1]2[CH:5]=[CH:4][CH:3]=[N:2]2)=[CH:7][CH:8]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A round-bottomed flask was charged with 4-pyrazole-1-yl-phenol (175 mg, 1.09 mmol), and 3.6 ml of toluene, triphenylphosphine (430 mg, 1.64 mmol), and benzyl N-(2-hydroxyethyl)carbamate (320 mg, 1.64 mmol) were then added. The solution was cooled to 0° C. and 1,1′-(azodicarbonyl)-dipiperidine (414 mg, 1.64 mmol) was added. The mixture was allowed to stir for about ten minutes at about 0° C. and was then allowed to warm to room temperature. An additional 3.6 ml of toluene and 3.6 ml of tetrahydrofuran were added to the viscous solution. The reaction mixture was stirred for about forty-eight hours, and the precipitated solids were filtered off and washed with a minimum volume of 1:1 toluene/tetrahydrofuran. The filtrate was concentrated in vacuo to afford the intermediate [2-(4-pyrazole-1-yl-phenoxy)-ethyl]-carbamic acid benzyl ester as an oil which was used directly in the next step.

Workup

additionwere then added
temperatureto warm to room temperature
stirringThe reaction mixture was stirred for about forty-eight hours
filtrationthe precipitated solids were filtered off
washwashed with a minimum volume of 1:1 toluene/tetrahydrofuran
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-d24d7bd001ea492fa9a7c85101b14489
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06566377B2

Reaction notes

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