HCID 178470407, compound → HCID 178470408, compound

HRID 1675910Notes

Reaction equation

HRID 1675910 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:33][N:32]=[C:31]2[C:7]=1[CH2:8][CH:9]1[CH:22]3[CH:13]([C:14]4[CH:15]=[CH:16][C:17]([O:23]CC5C=CC=CC=5)=[CH:18][C:19]=4[CH2:20][CH2:21]3)[CH2:12][CH2:11][C:10]12[CH3:34])=[O:5])[CH3:2]>[Pd].C1COCC1.C(O)C>[CH2:1]([O:3][C:4]([C:6]1[NH:33][N:32]=[C:31]2[C:7]=1[CH2:8][CH:9]1[CH:22]3[CH:13]([C:14]4[CH:15]=[CH:16][C:17]([OH:23])=[CH:18][C:19]=4[CH2:20][CH2:21]3)[CH2:12][CH2:11][C:10]12[CH3:34])=[O:5])[CH3:2]

Participants

5

Reactant 1

HCID 178470407HCID 178470407, compound

Product 1

HCID 178470408HCID 178470408, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Palladium on charcoal (100 mg, 5%Pd) was added to a solution of 2-Benzyloxy-6a-methyl-4b,5,6,6a,8,10,10a,10b,11,12-decahydro-7,8-diaza-pentaleno[2,1-a]phenanthrene-9-carboxylic acid ethyl ester (913 mg, 2.0 mmol, CAB03049) in THF (30 mL) and ethanol (30 mL). The resulting mixture was stirred under a hydrogen-atmosphere (balloon) for 72 hours, filtered through a 3 cm layer of celite and concentrated under reduced pressure. The residue was crystallised from acetone/cyclohexane. Yield: 602 mg (82%) pale yellow crystals. 1H-NMR (DMSO-d6, 400 MHz), δ: 0.92 (s, 3H, —CH3), 1.12-2.84 (m, 16H), 4.14-4.40 (m, 2H, OCH2CH3), 6.45 (d, J=2.3 Hz, 1H), 6.50 (dd, J=8.6, 2.3 Hz, 1H), 7.05,(d, J=8.6 Hz, 1H), 9.01 (s, 1H, —OH), 13.07 (s, 1H, NH). LRMS (FAB+): 367.2 (100, [M+H]+). HRMS (FAB+): 367.203796 C22H27N2O3 requires 367.202168

Workup

  1. filtrationfiltered through a 3 cm layer of celite and
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was crystallised from acetone/cyclohexane

Sources & evidence

ORD record
ord-7af02abdea394ec6875f58c5b36f28f5
Source dataset
uspto-grants-2011_08
Patent number
US08003783B2

Reaction notes

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