HCID 67776369, compound → HCID 67774119, compound

HRID 406858Notes

Reaction equation

HRID 406858 reaction equation
[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C@@H:4]([CH2:5][CH2:6][C@:7]3([CH3:32])[CH:16]2[CH2:15][CH2:14][C@H:13]2[C@@:8]3([CH3:31])[CH2:9][CH2:10][C@@:11]3([C:27]([O:29][CH3:30])=[O:28])[CH2:23][CH2:22][C@@H:21]([C:24]([CH3:26])=[CH2:25])[C@@H:12]32)[C:3]1([CH3:34])[CH3:33].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[CH3:31][C@:8]12[C@@:7]3([CH3:32])[CH:16]([C@:17]4([CH3:20])[C@@H:4]([CH2:5][CH2:6]3)[C:3]([CH3:33])([CH3:34])[C:2](=[O:1])[CH2:19][CH2:18]4)[CH2:15][CH2:14][C@@H:13]1[C@H:12]1[C@H:21]([C:24]([CH3:26])=[CH2:25])[CH2:22][CH2:23][C@:11]1([C:27]([O:29][CH3:30])=[O:28])[CH2:10][CH2:9]2

Participants

4

Reactant 2

HCID 67776369HCID 67776369, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 67774119HCID 67774119, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1R,3aS,5aR,5bR,7aR,9S,11aR,13aR,13bR)-methyl 9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxylate (4 g, 8.50 mmol) in CH2Cl2 (100 mL) was added PCC (5.50 g, 25.5 mmol). The reaction mixture was stirred for 15 hours at room temperature. TLC indicated starting material was consumed and a new compound was generated. The reaction mixture was concentrated under reduced pressure and the residue was purified by biotage using ethyl acetate/hexanes (0-20%) to give the desired product (1R,3aS,5aR,5bR,7aR,11aR,13aR,13bR)-methyl 5a,5b,8,8,11a-pentamethyl-9-oxo-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxylate as a white solid (4 g, 100%). 1H NMR (500 MHz, DMSO-D6) δ ppm 0.85 (s, 3H), 0.88 (s, 3H), 0.93 (s, 3H), 0.95 (s, 3H), 0.98 (s, 3H), 1.00-1.64 (m, 17H), 1.65 (s, 3H), 1.73-1.84 (m, 3H), 2.07-2.23 (m, 2H), 2.28-2.39 (m, 1H), 2.39-2.48 (m, 1H), 2.86-3.00 (m, 1H), 3.56-3.63 (s, 3H), 4.58 (s, 1H), 4.71 (d, J=1.83 Hz, 1H).

Workup

  1. customwas consumed
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by biotage

Sources & evidence

ORD record
ord-fee1fbfe991644f5ae9655f13819f321
Source dataset
uspto-grants-2014_06
Patent number
US08754068B2

Reaction notes

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