Benzyl Alcohol → (1-Phenyl-cyclohexyl)-carbamic acid benzyl ester

HRID 2235198Notes

Reaction equation

[C:1]1([C:7]2(C(O)=O)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([N:18]([CH2:21]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:30])C=CC=CC=1.[CH2:40]([OH:47])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>C1C=CC=CC=1>[CH2:40]([O:47][C:21](=[O:30])[NH:18][C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Dissolve 1-phenyl-cyclohexanecarboxylic acid (5.0 g, 24.48 mmol) in benzene (200 mL). Add triethylamine (2.45 g, 24.48 mmol), diphenylphosphoryl azide (6.74 g, 24.48 mmol), and benzyl alcohol (3.97 g, 36.72 mmol) under nitrogen. Stir and heat the reaction mixture to 80° C. Continue to heat the reaction at 80° C. for 8 hours, then cool to room temperature. Add water (250 mL), and extract the aqueous layer with ethyl acetate (3×300 mL). Combine the organic layers and dry with Na2SO4, filter, concentrate and purify by flash column chromatography (silica gel, 5-25% of EtOAc/Hexane) to give 2.87 g (38%) of the title compound as a colorless oil.

Workup

temperatureto heat
customthe reaction at 80° C. for 8 hours
temperaturecool to room temperature
extractionAdd water (250 mL), and extract the aqueous layer with ethyl acetate (3×300 mL)
dry with materialCombine the organic layers and dry with Na2SO4
filtrationfilter
concentrationconcentrate
custompurify by flash column chromatography (silica gel, 5-25% of EtOAc/Hexane)

Sources & evidence

ORD record: ord-2fbe188cdd314f84b899a53aec685cf6
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07713979B2

Reaction notes

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