HCID 86586010, compound → HCID 86586009, compound

HRID 843691Notes

Reaction equation

HRID 843691 reaction equation
[CH3:1][O:2][C:3](=[O:64])[C@H:4]1[O:51][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[CH2:50][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:53](=[O:55])[CH3:54])([OH:52])[C@@:6]([C:57](=[O:59])[CH3:58])([OH:56])[C@@H:5]1[O:60][C:61](=[O:63])[CH3:62]>C1COCC1.CO.[Pd]>[CH3:1][O:2][C:3](=[O:64])[C@H:4]1[O:51][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][CH2:50]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:53](=[O:55])[CH3:54])([OH:52])[C@@:6]([C:57](=[O:59])[CH3:58])([OH:56])[C@@H:5]1[O:60][C:61](=[O:63])[CH3:62]

Participants

4

Reactant 1

HCID 86586010HCID 86586010, compound

Product 1

HCID 86586009HCID 86586009, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Glycosidated indole 34 (3.7 g, 4.2 mmol) in 60 mL THF/MeOH (1:1) was treated with 10% Pd/C (1.5 g) and hydrogenated in a Parr apparatus at 40 psi for 23 h. The reaction mixture was filtered through a bed of Celite and the filter cake was washed with THF (20 mL) and EtOH (20 mL). To avoid any air oxidation, L-ascorbic acid (0.37 g) was added to the filtered solution. The solution was concentrated and chromatographed on silica gel using CHCl3/i-PrOH (7:1) to render the product 35 (1.6 g, 48%) as a brown foam: Rf=0.20 (7:1 CHCl3:iPrOH); 1H NMR (DMSO) 6.5-7.5 (m, 11H), 5.7 (d, 1H, J=7.9 Hz), 5.5 (t, 1H, J=9.6 Hz), 4.9-5.2 (m, 4H), 4.7 (d, 1H, J=9.9 Hz), 3.6 (s, 3H), 3.3 (s, 8H), 2.1 (s, 3H), 1.9-2.2 (m, 9H), 1.5-1.9 (m, 8H); 13C NMR (CDCl3) 170.0, 169.0, 167.0, 157.0, 156.5, 150.0, 138.0, 131.7, 131.6, 130.0, 127.3, 116.9, 114.7, 112.0, 111.0, 108.0, 104.5, 98.8, 72.6, 71.8, 71.1, 69.1, 64.4, 55.0, 55.2, 53.0, 47.0, 26.7, 23.6, 20.6, 20.5, 9.5; IR (KBr): νmax 3427, 3037, 2935, 2612, 1757, 1612, 1510, 1462, 1374, 1227, 1040 cm−1; LC/MS (ESI) retention time=13.0, M+H+=787.

Workup

  1. filtrationThe reaction mixture was filtered through a bed of Celite
  2. washthe filter cake was washed with THF (20 mL) and EtOH (20 mL)
  3. additionwas added to the filtered solution
  4. concentrationThe solution was concentrated
  5. customchromatographed on silica gel

Sources & evidence

ORD record
ord-ef5fbbd80dce4017b39b7dbc7d3b4138
Source dataset
uspto-grants-2002_04
Patent number
US06380166B1

Reaction notes

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