HCID 67776210, compound → HCID 67776673, compound

HRID 405050Notes

Reaction equation

HRID 405050 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[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]([CH3:32])([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 67776210HCID 67776210, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 67776673HCID 67776673, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-3a-yl)methyl benzoate (8.6 g, 15.73 mmol) in CH2Cl2 (100 ml) was added PCC (5.09 g, 23.59 mmol). After 7.25 h of stirring at rt, the mixture was filtered through a pad of celite and silica gel and was washed with dichloromethane then with 1:1 EtOAc:hexanes. The filtrate was concentrated under reduced pressure to give the title compound as a white foam (8.26 g, 15.16 mmol, 96% yield). 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 8.05 (d, J=7.32 Hz, 2H),7.56 (t, J=7.48 Hz, 1H), 7.44 (t, J=7.63 Hz, 2H), 4.72 (s, 1H), 4.61 (s, 1H), 4.52 (d, J=10.99 Hz, 1H), 4.09 (d, J=11.29 Hz, 1H), 2.45-2.58 (m, 2H), 2.34-2.43 (m, 1H), 1.86-2.10 (m, 4H), 1.70 (s, 3H), 1.10 (s, 3H), 1.06 (s, 3H), 1.04-1.82 (m, 18H), 1.02 (s, 3H), 1.01 (s, 3H), 0.94 (s, 3H).

Workup

  1. filtrationthe mixture was filtered through a pad of celite and silica gel
  2. washwas washed with dichloromethane
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-81511a33b4a94a7c89d5e65fc940d25e
Source dataset
uspto-grants-2014_06
Patent number
US08748415B2

Reaction notes

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