Acetic Acid → ethyl 4-((1S,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-amino-1-isopropyl-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]chrysen-9-yl)cyclohex-3-enecarboxylate

HRID 1400982Notes

Reaction equation

HRID 1400982 reaction equation
[NH2:1][C@:2]12[CH2:38][CH2:37][C@@H:36]([C:39]([CH3:41])=[CH2:40])[C@@H:3]1[C@@H:4]1[C@@:17]([CH3:20])([CH2:18][CH2:19]2)[C@@:16]2([CH3:21])[C@@H:7]([C@:8]3([CH3:35])[C@@H:13]([CH2:14][CH2:15]2)[C:12]([CH3:23])([CH3:22])[C:11]([C:24]2[CH2:29][CH2:28][CH:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:26][CH:25]=2)=[CH:10][CH2:9]3)[CH2:6][CH2:5]1.C(O)(=O)C>C(O)C.O1CCOCC1.[Pd]>[NH2:1][C@:2]12[CH2:38][CH2:37][C@@H:36]([CH:39]([CH3:40])[CH3:41])[C@@H:3]1[C@@H:4]1[C@@:17]([CH3:20])([CH2:18][CH2:19]2)[C@@:16]2([CH3:21])[C@@H:7]([C@:8]3([CH3:35])[C@@H:13]([CH2:14][CH2:15]2)[C:12]([CH3:22])([CH3:23])[C:11]([C:24]2[CH2:29][CH2:28][CH:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:26][CH:25]=2)=[CH:10][CH2:9]3)[CH2:6][CH2:5]1

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 86692333ethyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-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)cyclohex-3-enecarboxylate

Product 1

HCID 86692332ethyl 4-((1S,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-amino-1-isopropyl-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]chrysen-9-yl)cyclohex-3-enecarboxylateYield 100%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of ethyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-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)cyclohex-3-enecarboxylate (0.1 g, 0.178 mmol) in ethanol (5 mL), 1,4-dioxane (2 mL) and acetic acid (0.051 mL, 0.890 mmol) was added 10% palladium on carbon (0.095 g, 0.089 mmol). The mixture was evacuated and refilled with nitrogen three times then was stirred under 1 atmosphere of hydrogen gas for 16 h. The mixture was evacuated and flushed with nitrogen, then was filtered through celite and was concentrated under reduced pressure to give the expected product (0.100 g, 0.178 mmol, 100% yield) as an off-white solid. 1H NMR (400 MHz, chloroform-d) δ=5.36 (br. s., 1H), 5.19 (d, J=5.8 Hz, 1H), 4.19-4.11 (m, 2H), 2.57-2.47 (m, 1H), 2.31 (dd, J=2.9, 2.1 Hz, 2H), 2.17 (dd, J=4.6, 2.6 Hz, 2H), 2.12-0.70 (m, 52H).

Workup

  1. customThe mixture was evacuated
  2. additionrefilled with nitrogen three times
  3. customThe mixture was evacuated
  4. customflushed with nitrogen
  5. filtrationwas filtered through celite
  6. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-2618f5d0c41f44e6ace1a1d833dc5d91
Source dataset
uspto-grants-2014_12
Patent number
US08906889B2

Reaction notes

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