N,N,N',N'-Tetramethylazodicarboxamide → HCID 66817356, compound

HRID 1755034Notes

Reaction equation

[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].[CH2:7]([O:14][C:15]([CH:17]1[CH2:22][CH2:21][CH:20]([CH2:23]O)[CH2:19][CH2:18]1)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.N(C(N(C)C)=O)=NC(N(C)C)=O.C(P(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[CH2:7]([O:14][C:15]([CH:17]1[CH2:22][CH2:21][CH:20]([CH2:23][O:4][CH2:3][C:2]([F:6])([F:5])[F:1])[CH2:19][CH2:18]1)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 65 °C

Procedure

2,2,2-Trifluoro-ethanol (288 μL, 4.03 mmol) was added to a mixed solution of 4-hydroxymethyl-cyclohexanecarboxylic acid benzyl ester (100 mg, 0.403 mmol), 1,1′-azobis(N,N-dimethylformamide) (139 mg, 0.805 mmol) and tributyl-phosphine (199 μL, 0.805 mmol) in toluene (1.2 mL) at 0° C. The mixture was stirred at 65° C. for 1.5 hours and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 4-(2,2,2-trifluoro-ethoxymethyl)-cyclohexanecarboxylic acid benzyl ester as a colorless liquid (126 mg, 95%).

Workup

concentrationconcentrated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-c5bc92f55c64412f9e22cbd5522c0840
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09169254B2

Reaction notes

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