HCID 330750, compound → HCID 49864296, compound

HRID 1677837Notes

Reaction equation

HRID 1677837 reaction equation
[CH3:1][C@@H:2]1[C:31]([CH3:33])([CH3:32])[O:30][C@@:4]2([O:8][C@H:7]3[CH2:9][C@H:10]4[C@@H:15]5[CH2:16][CH2:17][C@H:18]6[CH2:23][C@H:22]([OH:24])[CH2:21][CH2:20][C@:19]6([CH3:25])[C@H:14]5[C@@H:13]([OH:26])[CH2:12][C@:11]4([CH3:27])[C@H:6]3[C@:5]2([OH:29])[CH3:28])[CH2:3]1.[CH3:34][C@@H:35]1[C:64]([CH3:66])([CH3:65])[O:63][C@:37]2([O:41][C@H:40]3[CH2:42][C@H:43]4[C@@H:48]5[CH2:49][CH2:50][C@H:51]6[CH2:56][C@H:55]([OH:57])[CH2:54][CH2:53][C@:52]6([CH3:58])[C@H:47]5[C@@H:46]([OH:59])[CH2:45][C@:44]4([CH3:60])[C@H:39]3[C@:38]2([OH:62])[CH3:61])[CH2:36]1>>[CH3:1][C@@H:2]1[C:31]([CH3:32])([CH3:33])[O:30][C@@:4]2([O:8][C@H:7]3[CH2:9][C@H:10]4[C@@H:15]5[CH2:16][CH2:17][C@H:18]6[CH2:23][C@H:22]([OH:24])[CH2:21][CH2:20][C@:19]6([CH3:25])[C@H:14]5[C:13](=[O:26])[CH2:12][C@:11]4([CH3:27])[C@H:6]3[C@:5]2([OH:29])[CH3:28])[CH2:3]1.[CH3:34][C@@H:35]1[C:64]([CH3:65])([CH3:66])[O:63][C@@:37]2([O:41][C@H:40]3[CH2:42][C@H:43]4[C@@H:48]5[CH2:49][CH2:50][C@H:51]6[CH2:56][C:55](=[O:57])[CH2:54][CH2:53][C@:52]6([CH3:58])[C@H:47]5[C:46](=[O:59])[CH2:45][C@:44]4([CH3:60])[C@H:39]3[C@:38]2([OH:62])[CH3:61])[CH2:36]1

Participants

4

Reactant 2

HCID 330750HCID 330750, compoundHCID 9981822Hippuristanol

Product 2

HCID 11453970HCID 11453970, compoundYield 40%HCID 49864296HCID 49864296, compoundYield 45%

Procedure

Oxidation of epihippuristanol (10) to give epihippuristanol 11-one (13) and epihippuristanol 3,11-dione (14). Epihippuristanol (10, 31.4 mg) was oxidized in the same fashion as described above for hippuristanol (1). The crude product was separated by TLC (CHCl3/EtOAc, 1:1, v/v) to give 12.6 mg of epihippuristanol 11-one (13, 40%) and 14.0 mg of epihippuristanol 3,11-dione (14, 45%). Epihippuristanol 3,11-dione (14). white crystals, mp 226-229° C.; 1H NMR (CDCl3) δ 4.48 (brq, J=7.0 Hz, 1H), 2.82 (ddd, J=13, 6.5, 2 Hz, 1H), 2.57 (d, J=12 Hz, 1H), 2.45 (dt, J=6.5, 14 Hz, 1H), 1.30 (s, 3H), 1.28 (s, 3H), 1.22 (s, 3H), 1.08 (s, 3H), 0.98 (s, 3H), 0.94 (d, J=7 Hz, 3H); 13C NMR (CDCl3) δ 211.4, 209.9, 118.6, 84.5, 81.9, 79.0, 64.1, 63.2, 58.2, 55.8, 47.0, 45.9, 44.3, 41.0, 39.6, 38.0, 37.1, 35.8 (2C), 35.3, 32.3, 31.5, 29.0, 28.2, 26.0, 23.0, 17.6, 14.0, 11.1; IR (KBr) 3450, 1700 cm−1; EIMS m/z 458 (M+, 6), 443 (16), 400 (7), 330 (32), 315 (100%).

Workup

  1. customThe crude product was separated by TLC (CHCl3/EtOAc, 1:1

Sources & evidence

ORD record
ord-8098b90976394033ab18f45fda1c4f03
Source dataset
uspto-grants-2011_08
Patent number
US08008346B2

Reaction notes

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