(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 → (1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a-formyl-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

HRID 1401017Notes

Reaction equation

[F:1][C:2]([F:48])([F:47])[S:3]([O:6][C:7]1[C:8]([CH3:46])([CH3:45])[C@H:9]2[C@:22]([CH3:25])([CH2:23][CH:24]=1)[C@@H:21]1[C@:12]([CH3:44])([C@@:13]3([CH3:43])[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(NCCN1CCS(=O)(=O)CC1)[CH2:15][CH2:14]3)[CH2:11][CH2:10]2)(=[O:5])=[O:4].C[C@]12[C@@]3(C)[C@@H]([C@]4(C)[C@@H](CC3)C(C)(C)[C:62](=[O:71])CC4)CCC1[C@H]1[C@H](C(C)=C)CC[C@]1(C=O)CC2>>[F:48][C:2]([F:47])([F:1])[S:3]([O:6][C:7]1[C:8]([CH3:46])([CH3:45])[C@H:9]2[C@:22]([CH3:25])([CH2:23][CH:24]=1)[C@@H:21]1[C@:12]([CH3:44])([C@@:13]3([CH3:43])[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([CH:62]=[O:71])[CH2:15][CH2:14]3)[CH2:11][CH2:10]2)(=[O:4])=[O:5]

Participants

Reactant 2

HCID 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

HCID 86692373(1R,3aS,5aR,5bR,7aR,11aR,11bR,13bR)-5a,5b,8,8,11a-pentamethyl-9-oxo-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carbaldehyde

Product 1

HCID 86692374(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a-formyl-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 trifluoromethanesulfonateYield 71%

Procedure

The title compound was prepared following the procedure described in method 1 for the preparation of intermediate 1, Step 5, using (1R,3aS,5aR,5bR,7aR,11aR,11bR,13bR)-5a,5b,8,8,11a-pentamethyl-9-oxo-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carbaldehyde as the starting material. (71% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ 9.69 (d, J=1.8 Hz, 1H), 5.58 (dd, J=6.7, 2.1 Hz, 1H), 4.89-4.54 (m, 2H), 2.90 (td, J=11.0, 5.8 Hz, 1H), 2.28-2.00 (m, 3H), 2.00-1.64 (m, 7H), 1.60-1.55 (m, 3H), 1.53-1.18 (m, 11H), 1.14 (s, 3H), 1.08 (d, J=7.8 Hz, 1H), 1.03 (s, 3H), 1.00 (s, 3H), 0.97 (s, 3H), 0.93 (s, 3H)

Sources & evidence

ORD record: ord-950e4d37d6c547289fc8a36fe5501fa0
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906889B2

Reaction notes

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