Methyl 2-(3-oxocyclopentyl)acetate → HCID 86692376, compound

HRID 1401020Notes

Reaction equation

HRID 1401020 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[CH2:54][CH2:53][CH:52]([CH2:55][C:56]([O:58][CH3:59])=[O:57])[CH2:51]1>>[F:1][C:2]([F:48])([F:47])[S:3]([O:49][C:50]1[CH2:51][CH:52]([CH2:55][C:56]([O:58][CH3:59])=[O:57])[CH2:53][CH:54]=1)(=[O:5])=[O:4]

Participants

3

Reactant 2

HCID 11355614Methyl 2-(3-oxocyclopentyl)acetateHCID 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 1

HCID 86692376HCID 86692376, compoundYield 50.1%

Procedure

The title compound was prepared following the procedure described in method 2 for the preparation of intermediate 1, Step 6, using methyl 2-(3-oxocyclopentyl)acetate as the reactant. (50.1% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ 5.66 (q, J=2.1 Hz, 1H), 3.73 (br. s., 3H), 3.29-3.13 (m, 1H), 2.95-2.78 (m, 1H), 2.67-2.57 (m, 2H), 2.49-2.40 (m, 1H), 2.40-2.28 (m, 1H), 1.77-1.63 (m, 1H). 19F NMR (376 MHz, CHLOROFORM-d) δ −73.53 (s, 3F).

Sources & evidence

ORD record
ord-4692fe5a38d44872bfa284624632881b
Source dataset
uspto-grants-2014_12
Patent number
US08906889B2

Reaction notes

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