HCID 67776653, compound → HCID 67952353, compound

HRID 406898Notes

Reaction equation

HRID 406898 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]([CH3:49])([CH3:48])[CH:13]3[C:26]([CH3:29])([CH2:27][CH:28]=2)[CH:25]2[C:16]([CH3:47])([C:17]4([CH3:46])[CH:22]([CH2:23][CH2:24]2)[CH:21]2[CH:30]([C:33]([CH3:35])=[CH2:34])[CH2:31][CH2:32][C:20]2([C:36]([O:38][Si:39]([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40])=[O:37])[CH2:19][CH2:18]4)[CH2:15][CH2:14]3)=[CH:7][CH:6]=1)=[O:4]>[Pd]>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[C:12]([CH3:48])([CH3:49])[C@H:13]3[C@:26]([CH3:29])([CH2:27][CH:28]=2)[C@@H:25]2[C@:16]([CH3:47])([C@@:17]4([CH3:46])[C:22](=[CH:23][CH2:24]2)[C@H:21]2[C@:20]([C:36]([O:38][Si:39]([C:42]([CH3:44])([CH3:43])[CH3:45])([CH3:41])[CH3:40])=[O:37])([CH2:32][CH2:31][C:33]([CH3:34])([CH3:35])[CH2:30]2)[CH2:19][CH2:18]4)[CH2:15][CH2:14]3)=[CH:9][CH:10]=1)=[O:4]

Participants

3

Reactant 1

HCID 67776653HCID 67776653, compound

Product 1

HCID 67952353HCID 67952353, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Palladium catalyzed hydrosilylation of the benzyl esters intermediate B4 as described in the preparation of 1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-tert-butyldimethylsilyl 9-(4-(methoxycarbonyl)phenyl)-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]chrysene-3a-carboxylate, (intermediate 5) afforded the title compound (54%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.25 (s, 3H), 0.26 (s, 3H), 0.87 (s, 3H), 0.92 (s, 3H), 0.93-0.97 (m, 18H), 1.07 (s, 3H), 1.12-1.17 (m, 2H), 1.18 (s, 4H), 1.21-1.30 (m, 3H), 1.30-1.53 (m, 5H), 1.62-1.80 (m, 5H), 1.82-1.95 (m, 1H), 1.95-2.03 (m, 2H), 2.07 (dd, J=17.07, 6.27 Hz, 1H), 2.88 (dd, J=13.93, 4.64 Hz, 1H), 3.92 (s, 3H), 5.31 (dd, J=6.27, 1.76 Hz, 1H), 5.35 (t, J=3.51 Hz, 1H), 7.22 (d, J=8.53 Hz, 2H), 7.94 (d, J=8.28 Hz, 2H).

Sources & evidence

ORD record
ord-130ab72dd9e046a89a36267541732514
Source dataset
uspto-grants-2014_06
Patent number
US08754068B2

Reaction notes

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