HCID 67775380, compound → HCID 67776673, compound

HRID 406882Notes

Reaction equation

HRID 406882 reaction equation
[C:1]([O:9][CH2:10][C@:11]12[CH2:37][CH2:36][C@@H:35]([C:38]([CH3:40])=[CH2:39])[C@@H:12]1[CH:13]1[C@@:26]([CH3:29])([CH2:27][CH2:28]2)[C@@:25]2([CH3:30])[C@@H:16]([C@:17]3([CH3:34])[C@@H:22]([CH2:23][CH2:24]2)[C:21]([CH3:32])([CH3:31])[C@@H:20]([OH:33])[CH2:19][CH2:18]3)[CH2:15][CH2:14]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[C:1]([O:9][CH2:10][C@:11]12[CH2:37][CH2:36][C@@H:35]([C:38]([CH3:40])=[CH2:39])[C@@H:12]1[C@@H:13]1[C@@:26]([CH3:29])([CH2:27][CH2:28]2)[C@@:25]2([CH3:30])[C@@H:16]([C@:17]3([CH3:34])[C@@H:22]([CH2:23][CH2:24]2)[C:21]([CH3:31])([CH3:32])[C:20](=[O:33])[CH2:19][CH2:18]3)[CH2:15][CH2:14]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 67775380HCID 67775380, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 67776673HCID 67776673, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The crude material containing ((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-3a-yl)methyl benzoate (2.98 g, 5.45 mmol) from page above was dissolved in CH2Cl2 (50 ml) and treated with PCC (1.762 g, 8.18 mmol). The mixture was stirred at rt for 2 h. TLC showed no starting material and one less polar product. The mixture was filtered through celite and silica gel and the filtrate was concentrated in vacuo to afford the title compound as a white solid

Workup

  1. filtrationThe mixture was filtered through celite and silica gel
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-703be3e839994d2f918ab76dc024f097
Source dataset
uspto-grants-2014_06
Patent number
US08754068B2

Reaction notes

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