HCID 86586008, compound → HCID 86586007, compound

HRID 843690Notes

Reaction equation

HRID 843690 reaction equation
[CH3:1][O:2][C:3](=[O:63])[C@H:4]1[O:50][C@@H:8]([O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[N:17]([CH2:34][C:35]4[CH:40]=[CH:39][C:38]([O:41][CH2:42][CH2:43][N:44]5[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45]5)=[CH:37][CH:36]=4)[C:18]4[C:23]([C:24]=3[CH3:25])=[CH:22][C:21]([O:26]CC3C=CC=CC=3)=[CH:20][CH:19]=4)=[CH:12][CH:11]=2)[C@:7]([C:52](=[O:54])[CH3:53])([OH:51])[C@@:6]([C:56](=[O:58])[CH3:57])([OH:55])[C@@H:5]1[O:59][C:60](=[O:62])[CH3:61]>C1COCC1.CO.[Pd]>[CH3:1][O:2][C:3](=[O:63])[C@H:4]1[O:50][C@@H:8]([O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[N:17]([CH2:34][C:35]4[CH:36]=[CH:37][C:38]([O:41][CH2:42][CH2:43][N:44]5[CH2:45][CH2:46][CH2:47][CH2:48][CH2:49]5)=[CH:39][CH:40]=4)[C:18]4[C:23]([C:24]=3[CH3:25])=[CH:22][C:21]([OH:26])=[CH:20][CH:19]=4)=[CH:12][CH:11]=2)[C@:7]([C:52](=[O:54])[CH3:53])([OH:51])[C@@:6]([C:56](=[O:58])[CH3:57])([OH:55])[C@@H:5]1[O:59][C:60](=[O:62])[CH3:61]

Participants

4

Reactant 1

HCID 86586008HCID 86586008, compound

Product 1

HCID 86586007HCID 86586007, compoundYield 98.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Glycosidated indole 33 (34 g, 0.039 mol) in 400 mL THF/MeOH (1:1) was treated with 10% Pd/C (5.4 g) and hydrogenated in a Parr apparatus at 50 psi for 30 h. The mixture was filtered through Siluflock and 0.34 g of L-Ascorbic acid was added to the filtrate. The cake of Siluflock was washed with THF and the combined filtrates were concentrated to yield product 35 (29.8 g, 98%) as a yellowish-white solid: 1H NMR (CDCl3) δ 6.95 (m, 11 H), 5.34 (m, 2 H), 5.14 (d, 1 H, J=2 Hz), 5.01 (s, 2 H), 4.21 (m, 1 H), 4.06 (t, 2 H), 2.83 (t, 2 H), 2.62 (br s, 4 H), 2.13 (s, 3 H), 1.65 (t, 4 H), 1.44 (br s, 2 H).

Workup

  1. filtrationThe mixture was filtered through Siluflock and 0.34 g of L-Ascorbic acid
  2. additionwas added to the filtrate
  3. washThe cake of Siluflock was washed with THF
  4. concentrationthe combined filtrates were concentrated

Sources & evidence

ORD record
ord-ddb6eb0ef13b48e4a23ad4ecde473aff
Source dataset
uspto-grants-2002_04
Patent number
US06380166B1

Reaction notes

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