Tetrabutylammonium Fluoride → HCID 67777459, compound

HRID 2405504Notes

Reaction equation

HRID 2405504 reaction equation
[CH:1]([C@H:4]1[C@@H:8]2[C@@H:9]3[C@@:22]([CH3:25])([CH2:23][CH2:24][C@@:7]2([C:40]([O:42]CC2C=CC=CC=2)=[O:41])[CH2:6][CH2:5]1)[C@@:21]1([CH3:26])[C@@H:12]([C@:13]2([CH3:39])[C@@H:18]([CH2:19][CH2:20]1)[C:17]([CH3:28])([CH3:27])[C:16]([C:29]1[CH:34]=[CH:33][C:32]([C:35]([O:37][CH3:38])=[O:36])=[CH:31][CH:30]=1)=[CH:15][CH2:14]2)[CH2:11][CH2:10]3)([CH3:3])[CH3:2].C([SiH](C)C)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C(Cl)Cl.O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:1]([C@H:4]1[C@@H:8]2[C@@H:9]3[C@@:22]([CH3:25])([CH2:23][CH2:24][C@@:7]2([C:40]([OH:42])=[O:41])[CH2:6][CH2:5]1)[C@@:21]1([CH3:26])[C@@H:12]([C@:13]2([CH3:39])[C@@H:18]([CH2:19][CH2:20]1)[C:17]([CH3:28])([CH3:27])[C:16]([C:29]1[CH:30]=[CH:31][C:32]([C:35]([O:37][CH3:38])=[O:36])=[CH:33][CH:34]=1)=[CH:15][CH2:14]2)[CH2:11][CH2:10]3)([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 5072427tert-ButyldimethylsilaneHCID 67776064HCID 67776064, compound

Product 1

HCID 67777459HCID 67777459, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of (1S,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-benzyl 1-isopropyl-9-(4-(methoxycarbonyl)phenyl)-5a,5b,8,8,11a-pentamethyl-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 (220 mg, 0.331 mmol), tert-butyldimethylsilane (77 mg, 0.662 mmol), TEA (0.074 mL, 0.529 mmol) and palladium (II) acetate (18.57 mg, 0.083 mmol) in DCM (2 mL) was heated up at 60° C. for 3 h, TLC indicated the starting material was consumed. The reaction mixture was filtered a pad of celite. The filtrates were concentrated under reduced pressure to provide the intermediate. To this intermediate in dioxane (2 mL) was added TBAF (346 mg, 0.993 mmol), the reaction mixture was stirred for 2 h at room temperature. LCMS indicated the formation of desired product. The reaction mixture was quenched with distilled water (5 mL), extracted with DCM (3×8 mL). All the extracts were combined, dried over sodium sulfate, filtered and concentrated under reduced pressure to provide the desired product as a pale yellow solid (150 mg, 79%). LCMS: m/e 575.35 (M+H)+, 2.84 min (method 1).

Workup

  1. customwas consumed
  2. filtrationThe reaction mixture was filtered a pad of celite
  3. concentrationThe filtrates were concentrated under reduced pressure
  4. customto provide the intermediate

Sources & evidence

ORD record
ord-16ed7c19dd5d49af9ab8bab9e33b304e
Source dataset
uspto-grants-2014_08
Patent number
US08802661B2

Reaction notes

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