HCID 66762819, compound → HCID 66761794, compound

HRID 573770Notes

Reaction equation

[Si:1]([O:8][C@H:9]1[CH2:18][C:17]([CH3:20])([CH3:19])[CH2:16][C:15]2[N:14]=[C:13]([CH:21]([CH3:23])[CH3:22])[C:12]3[C@@H:24]([C:31]4[CH:41]=[CH:40][C:34](C(OCC)=O)=[CH:33][CH:32]=4)[O:25][C:26]4([CH2:30][CH2:29][CH2:28][CH2:27]4)[C:11]=3[C:10]1=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C[Mg]Br>O1CCCC1.C1(C)C=CC=CC=1.O1CCCC1>[Si:1]([O:8][C@H:9]1[CH2:18][C:17]([CH3:19])([CH3:20])[CH2:16][C:15]2[N:14]=[C:13]([CH:21]([CH3:23])[CH3:22])[C:12]3[C@@H:24]([C:31]4[CH:32]=[CH:33][C:34]([C:9]([OH:8])([CH3:18])[CH3:10])=[CH:40][CH:41]=4)[O:25][C:26]4([CH2:30][CH2:29][CH2:28][CH2:27]4)[C:11]=3[C:10]1=2)([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: -5 °C

Procedure

110 mg Ethyl 4-((3′R,9′S)-9′-(tert-butyldimethylsilyloxy)-4′-isopropyl-7′,7′-dimethyl-6′,7′,8′,9′-tetrahydro-3′H-spiro[cyclopentane-1,1′-furo[3,4-c]quinoline]-3′-yl)benzoate are dissolved in 3 ml tetrahydrofurane, cooled to −5° C. and treated dropwise with 820 μl of a 1.4 M solution of methylmagnesium bromide in toluene/tetrahydrofurane (72:25). The mixture is warmed to room temperature during 1 hour, then recooled to 0° C. and the reaction is quenched by addition 1 ml methanol. The solvents are evaporated in vacuo and the residue is chromatographed on silica gel (petrole ether/ethylacetate 90:10 to 50:50).

Workup

temperatureThe mixture is warmed to room temperature during 1 hour
customrecooled to 0° C.
customthe reaction is quenched by addition 1 ml methanol
customThe solvents are evaporated in vacuo
customthe residue is chromatographed on silica gel (petrole ether/ethylacetate 90:10 to 50:50)

Sources & evidence

ORD record: ord-5d4c358e96424aed8009fa063fd663eb
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029544B2

Reaction notes

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