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6,9-Dihydroxy-8-methylene-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12]tetradeca-2,4,6-triene-4-carbaldehyde → 4-Hydroxymethyl-8-methyl-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12]tetradeca-2,4,6-triene-6,9-diol

HRID 1252424
Notes
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Reaction equation

HRID 1252424 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:18]=[O:19])[CH:5]=[C:6]2[C:14]=1[C:13](=[CH2:15])[C:12]1([OH:17])[O:16][N:7]2[CH2:8][CH:9]2[CH:11]1[NH:10]2>CO.[Pd].[H][H]>[OH:19][CH2:18][C:4]1[CH:5]=[C:6]2[C:14](=[C:2]([OH:1])[CH:3]=1)[CH:13]([CH3:15])[C:12]1([OH:17])[O:16][N:7]2[CH2:8][CH:9]2[CH:11]1[NH:10]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 1

HCID 150517286,9-Dihydroxy-8-methylene-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12]tetradeca-2,4,6-triene-4-carbaldehyde

Product 1

HCID 867413194-Hydroxymethyl-8-methyl-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12]tetradeca-2,4,6-triene-6,9-diol

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent
HCID 178418361
HCID 178418361, compound
Solvent

Procedure

6,9-Dihydroxy-8-methylene-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-triene-4-carbaldehyde (5 mg) was dissolved in methanol (2 ml), and the solution was subjected to catalytic reduction for 120 minutes using 10% palladium on carbon in hydrogen gas under atmospheric pressure at room temperature. The reaction mixture was filtered and the filtrate was evaporated to dryness to give an oily residue of 4-hydroxymethyl-8-methyl-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-triene-6,9-diol. This oil was dissolved in pyridine (1 ml) and to this solution was added acetic anhydride (20 μl), followed by allowing to stand at room temperature overnight. The resultant mixture was evaporated to dryness to give an oil, which was subjected to preparative thin layer chromatography. Development was carried out with a mixture of methanol and chloroform (5:95, v/v) to afford 4-acetoxymethyl-11-acetyl-9-hydroxy-8-methyl-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-trien-6-yl acetate (3 mg).

Workup

  1. customat room temperature
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-96edb4335b7f441c91936713306d99b6
Source dataset
uspto-grants-1988_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04743555

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes