Triethylsilane → HCID 50924549, compound

HRID 2179776Notes

Reaction equation

HRID 2179776 reaction equation
C([O:8][C:9]([C@@H:11]1[CH2:14][C@H:13]([C:15]([O:17][C@H:18]2[CH2:35][CH2:34][C@@:33]3([CH3:36])[C@@H:20]([CH2:21][CH2:22][C@:23]4([CH3:47])[C@@H:32]3[CH2:31][CH2:30][C@H:29]3[C@@:24]4([CH3:46])[CH2:25][CH2:26][C@@:27]4([C:43]([OH:45])=[O:44])[CH2:39][CH2:38][C@@H:37]([C:40]([CH3:42])=[CH2:41])[C@@H:28]43)[C:19]2([CH3:49])[CH3:48])=[O:16])[C:12]1([CH3:51])[CH3:50])=[O:10])C1C=CC=CC=1.[SiH](CC)(CC)CC>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:9]([C@@H:11]1[CH2:14][C@H:13]([C:15]([O:17][C@H:18]2[CH2:35][CH2:34][C@@:33]3([CH3:36])[C@@H:20]([CH2:21][CH2:22][C@:23]4([CH3:47])[C@@H:32]3[CH2:31][CH2:30][C@H:29]3[C@@:24]4([CH3:46])[CH2:25][CH2:26][C@@:27]4([C:43]([OH:45])=[O:44])[CH2:39][CH2:38][C@@H:37]([C:40]([CH3:42])=[CH2:41])[C@@H:28]43)[C:19]2([CH3:49])[CH3:48])=[O:16])[C:12]1([CH3:51])[CH3:50])([OH:10])=[O:8]

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 50924548HCID 50924548, compound

Product 1

HCID 50924549HCID 50924549, compoundYield 36.86%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-((1S,3R)-3-(benzyloxycarbonyl)-2,2-dimethylcyclobutanecarbonyloxy)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid (Example 18, 0.25 g) in dry DCM (10 ml) Et3N (5.77 ml) and Et3SiH (0.057 g) were added at about 0° C. then Pd(OAc)2 (0.005 g) was added under nitrogen conditions and the reaction mixture was stirred at reflux temperatures for over night. After completion of the reaction (monitored by TLC), the reaction mixture was diluted with DCM, and concentrated under reduced pressure, purified by column chromatography to afford the title compound (80 mg, 36.86% Yield). 1H NMR (300 MHz, CDCl3): δ 4.73 (1H, s), 4.54 (1H, s), 4.4-4.36 (1H, m), 3.0-2.90 (1H, m), 2.80-2.65 (2H, m), 2.6 (2H, m), 2.3-2.1 (3H, m), 2.0-1.88 (4H, m), 1.64 (5H, m), 1.61 (2H, m), 1.6-1.4 (4H, m), 1.39-1.3 (4H, m), 1.32 (6H, s), 1.3-1.02 (4H, m), 1.00 (3H, s),0.91 (3H, s), 0.89 (3H, s), 0.809 (3H, s), 0.790 (3H, s), 0.751 (3H, s); Mass: [M+Na]+ 633 (75%); 1R (KBr, cm−1): 3400, 2949, 1732, 1703, 1459, 1389, 1364, 1264, 1211, 1139, 1126, 1106, 1020, 942, 889. Melting Range: 308-310° C.

Workup

  1. temperatureat reflux temperatures for over night
  2. customAfter completion of the reaction (monitored by TLC)
  3. concentrationconcentrated under reduced pressure
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-8f6437dbe5c047e7a95f386a8ffde545
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

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