HCID 67350251, compound → HCID 11404563, compound

HRID 1675913Notes

Reaction equation

HRID 1675913 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[CH:13]3[CH:18]([CH2:19][CH2:20][C:21]=2[CH:22]=1)[CH:17]1[CH2:23][C:24]2[C:28]([C:16]1([CH3:31])[CH2:15][CH2:14]3)=[N:27][NH:26][C:25]=2[CH2:29][OH:30])C1C=CC=CC=1>[Pd].C1COCC1.C(O)C>[OH:30][CH2:29][C:25]1[NH:26][N:27]=[C:28]2[C:24]=1[CH2:23][CH:17]1[CH:18]3[CH:13]([C:12]4[CH:11]=[CH:10][C:9]([OH:8])=[CH:22][C:21]=4[CH2:20][CH2:19]3)[CH2:14][CH2:15][C:16]12[CH3:31]

Participants

5

Reactant 1

HCID 67350251HCID 67350251, compound

Product 1

HCID 11404563HCID 11404563, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Palladium on charcoal (50 mg, 5% Pd) was added to a solution (2-Benzyloxy-6a-methyl-4b,5,6,6a,8,10,10a,10b,11,12-decahydro-7,8-diaza-pentaleno[2,1-a]phenanthren-9-yl)-methanol (120 mg, 0.289 mmol, CAB03058) in THF (20 mL) and ethanol (20 mL). The resulting mixture was stirred under a hydrogen-atmosphere (balloon) for 24 hours, filtered through a 3 cm layer of celite and concentrated under reduced pressure. The residue was dried under high vacuum. Yield: 93 mg (99%) white solid. 1H-NMR (DMSO-d6, 270 MHz), δ: 0.82 (s, 3H, —CH3), 1.20-2.80 (m, 13H), 4.31 (s, 2H, —CH2OH), 4.95 (bs, 1H, —OH), 6.37 (s, 1H), 6.44 (d, J=8.5 Hz, 1H), 6.97 (d, J=8.5 Hz, 1H), 8.92 (s, 1H, —OH), 11.78 (bs, 1H, NH). LRMS (FAB+): 3.25.2 (100, [M]+). HRMS (FAB+): 325.192528 C20H25N2O2 requires 325.191603.

Workup

  1. filtrationfiltered through a 3 cm layer of celite and
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was dried under high vacuum

Sources & evidence

ORD record
ord-4cfd4bdcfb554adabd05b30c8f77d213
Source dataset
uspto-grants-2011_08
Patent number
US08003783B2

Reaction notes

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