(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-((2-(4-(methylsulfonyl)piperidin-1-yl)ethyl)amino)-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 → 8-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-((2-(4-(methylsulfonyl)piperidin-1-yl)ethyl)amino)-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)-2-oxaspiro[4.5]dec-7-en-1-one

HRID 1401015Notes

Reaction equation

FC(F)(F)S(O[C:7]1[C:8]([CH3:48])([CH3:47])[C@H:9]2[C@:22]([CH3:25])([CH2:23][CH:24]=1)[C@@H:21]1[C@:12]([CH3:46])([C@@:13]3([CH3:45])[C@H:18]([CH2:19][CH2:20]1)[C@H:17]1[C@H:26]([C:29]([CH3:31])=[CH2:30])[CH2:27][CH2:28][C@:16]1([NH:32][CH2:33][CH2:34][N:35]1[CH2:40][CH2:39][CH:38]([S:41]([CH3:44])(=[O:43])=[O:42])[CH2:37][CH2:36]1)[CH2:15][CH2:14]3)[CH2:11][CH2:10]2)(=O)=O.CC1(C)C(C)(C)OB([C:59]2[CH2:69][CH2:68][C:62]3([C:66](=[O:67])[O:65][CH2:64][CH2:63]3)[CH2:61][CH:60]=2)O1>>[CH3:45][C@:13]12[C@@:12]3([CH3:46])[C@@H:21]([C@:22]4([CH3:25])[C@@H:9]([CH2:10][CH2:11]3)[C:8]([CH3:48])([CH3:47])[C:7]([C:59]3[CH2:69][CH2:68][C:62]5([C:66](=[O:67])[O:65][CH2:64][CH2:63]5)[CH2:61][CH:60]=3)=[CH:24][CH2:23]4)[CH2:20][CH2:19][C@@H:18]1[C@H:17]1[C@H:26]([C:29]([CH3:31])=[CH2:30])[CH2:27][CH2:28][C@:16]1([NH:32][CH2:33][CH2:34][N:35]1[CH2:40][CH2:39][CH:38]([S:41]([CH3:44])(=[O:42])=[O:43])[CH2:37][CH2:36]1)[CH2:15][CH2:14]2

Participants

Reactant 2

HCID 71698667(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-((2-(4-(methylsulfonyl)piperidin-1-yl)ethyl)amino)-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

HCID 866923698-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-oxaspiro[4.5]dec-7-en-1-one

Product 1

HCID 866923708-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-((2-(4-(methylsulfonyl)piperidin-1-yl)ethyl)amino)-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)-2-oxaspiro[4.5]dec-7-en-1-oneYield 59%

Procedure

The title compound was prepared following the procedure described in general procedure Step 5, using (1R,3 aS,5aR,5bR,7aR,11aR,11bR,13 aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-((2-(4-(methylsulfonyl)piperidin-1-yl)ethyl)amino)-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 and 8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-oxaspiro[4.5]dec-7-en-1-one as reactants. The product was isolated as diastereomers (solid, 59% yield). MS: m/e 749.7 (M+H)+, 4.10 min (method 7). 1H NMR (400 MHz, CHLOROFORM-d) δ 5.35 (d, J=2.8 Hz, 1H), 5.24-5.19 (m, 1H), 4.72 (d, J=2.0 Hz, 1H), 4.59 (dd, J=2.3, 1.5 Hz, 1H), 4.37-4.25 (m, 2H), 3.12 (dd, J=14.6, 12.0 Hz, 2H), 2.87-2.78 (m, 1H), 2.84 (s, 3H), 2.67-2.53 (m, 3H), 2.50-2.40 (m, 3H), 2.33-0.90 (m, 35H), 1.70 (s, 3H), 1.09 (s, 3H), 0.98-0.92 (m, 6H), 0.96 (s, 3H), 0.86 (s, 3H).

Workup

customThe product was isolated as diastereomers (solid, 59% yield)
customm/e 749.7 (M+H)+, 4.10 min (method 7)

Sources & evidence

ORD record: ord-3dc963941a2f47b39972b061f475f4e9
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906889B2

Reaction notes

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