1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 71245714, compound

HRID 1472748Notes

Reaction equation

[OH:1][C:2]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([C:6]1[CH:10]=[CH:9][S:8][CH:7]=1)[C:3]([OH:5])=[O:4].N12CCCN=C1CCCCC2.S(O[CH2:39][CH:40]1[CH2:45][CH2:44][N:43]([C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[CH2:42][CH2:41]1)(C1C=CC(C)=CC=1)(=O)=O>C1(C)C=CC=CC=1.CN(C)C=O>[OH:1][C:2]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([C:6]1[CH:10]=[CH:9][S:8][CH:7]=1)[C:3]([O:5][CH2:39][CH:40]1[CH2:45][CH2:44][N:43]([C:46]([O:48][C:49]([CH3:50])([CH3:52])[CH3:51])=[O:47])[CH2:42][CH2:41]1)=[O:4]

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of 2-hydroxy-2-phenyl-2-(thiophen-3-yl)acetic acid (0.75 g, 3.197 mmol) in toluene (4 mL) and dimethyl formamide (0.4 mL), 1,8-diazabicyclo[5.4.0]undec-7-ene (735 μL, 4.919 mmol) was added followed by tert-butyl 4-(tosyloxymethyl)piperidine-1-carboxylate (0.909 g, 2.459 mmol) in toluene (3.5 ml) and dimethyl formamide (0.35 mL). The reaction mixture was heated at 100° C. overnight. After this time, the reaction mixture was cooled to RT and concentrated in vacuo. The crude mixture purified by silica gel column chromatography eluting with a gradient of iso-hexane:ethyl acetate (1:0 to 3:1) to afford the title compound (0.84 g, 79%).

Workup

temperatureAfter this time, the reaction mixture was cooled to RT
concentrationconcentrated in vacuo
customThe crude mixture purified by silica gel column chromatography
washeluting with a gradient of iso-hexane:ethyl acetate (1:0 to 3:1)

Sources & evidence

ORD record: ord-d56355ab84d749ffafce0000c1de5fd8
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012644B2

Reaction notes

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