Methyl 4-oxocyclohex-1-enecarboxylate → HCID 86692395, compound

HRID 1401035Notes

Reaction equation

HRID 1401035 reaction equation
[F:1][C:2]([F:48])([F:47])[S:3](OC1C(C)(C)[C@H]2[C@](C)(CC=1)[C@@H]1[C@](C)([C@@]3(C)[C@H](CC1)[C@H]1[C@H](C(C)=C)CC[C@]1(NCCN1CCS(=O)(=O)CC1)CC3)CC2)(=[O:5])=[O:4].[O:49]=[C:50]1[CH2:55][CH2:54][C:53]([C:56]([O:58][CH3:59])=[O:57])=[CH:52][CH2:51]1.[O:60]=[C:61]1[CH2:66][CH2:65][CH:64]([C:67]([O:69][CH3:70])=[O:68])[CH:63]=[CH:62]1>>[F:1][C:2]([F:48])([F:47])[S:3]([O:49][C:50]1[CH2:55][CH2:54][C:53]([C:56]([O:58][CH3:59])=[O:57])=[CH:52][CH:51]=1)(=[O:5])=[O:4].[O:60]=[C:61]1[CH2:66][CH2:65][C:64]([C:67]([O:69][CH3:70])=[O:68])=[CH:63][CH2:62]1.[O:49]=[C:50]1[CH2:55][CH2:54][CH:53]([C:56]([O:58][CH3:59])=[O:57])[CH:52]=[CH:51]1

Participants

6

Reactant 3

HCID 10855681Methyl 4-oxocyclohex-1-enecarboxylateHCID 11744838Methyl 4-oxocyclohex-2-enecarboxylateHCID 71698666(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a-((2-(1,1-dioxidothiomorpholino)ethyl)amino)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl trifluoromethanesulfonate

Product 3

HCID 10855681Methyl 4-oxocyclohex-1-enecarboxylateHCID 11744838Methyl 4-oxocyclohex-2-enecarboxylateHCID 86692395HCID 86692395, compoundYield 53.9%

Procedure

The title compound was prepared in 53.9% yield following the procedure described in step 6 of method 2 for the preparation of intermediate 1, using methyl 4-oxocyclohex-1-enecarboxylate and methyl 4-oxocyclohex-2-enecarboxylate as the reactants. Methyl 4-oxocyclohex-1-enecarboxylate and methyl 4-oxocyclohex-2-enecarboxylate were prepared following the procedures described in Tet. Lett. Vol. 53, issue 7, page 819-821. m/e 287.05 (M+H)+, 2.435 min (method 8). 1H NMR (400 MHz, CHLOROFORM-d) δ 6.96 (dt, J=6.3, 1.5 Hz, 1H), 6.07 (dt, J=6.4, 1.4 Hz, 1H), 3.78 (s, 3H), 2.81-2.73 (m, 2H), 2.67-2.59 (m, 2H). 19F NMR (376 MHz, CHLOROFORM-d) δ −73.55 (s, 3F).

Workup

  1. customm/e 287.05 (M+H)+, 2.435 min (method 8)

Sources & evidence

ORD record
ord-875efebb10524f98bb611595b363e8ef
Source dataset
uspto-grants-2014_12
Patent number
US08906889B2

Reaction notes

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