(4-Formyl-6,9-dihydroxy-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12]tetradeca-2(7),3,5-trien-8-yl)methyl carbamate → (7,9-Dihydroxy-5-(hydroxymethyl)-1,1a,2,8,9,9a-hexahydro-3,9-epoxyazireno(2,3-c)(1)benzazocin-8-yl)methyl hydrogen carbonimidate

HRID 1723367Notes

Reaction equation

HRID 1723367 reaction equation
[C:1](=[O:23])([O:3][CH2:4][CH:5]1[C:17]2([OH:19])[O:18][N:12]([CH2:13][CH:14]3[CH:16]2[NH:15]3)[C:11]2[C:6]1=[C:7]([OH:22])[CH:8]=[C:9]([CH:20]=[O:21])[CH:10]=2)[NH2:2]>CO.[Pd].[H][H]>[C:1](=[O:23])([O:3][CH2:4][CH:5]1[C:17]2([OH:19])[O:18][N:12]([CH2:13][CH:14]3[CH:16]2[NH:15]3)[C:11]2[C:6]1=[C:7]([OH:22])[CH:8]=[C:9]([CH2:20][OH:21])[CH:10]=2)[NH2:2]

Participants

5

Reactant 1

HCID 10448726(4-Formyl-6,9-dihydroxy-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12]tetradeca-2(7),3,5-trien-8-yl)methyl carbamate

Product 1

HCID 124136(7,9-Dihydroxy-5-(hydroxymethyl)-1,1a,2,8,9,9a-hexahydro-3,9-epoxyazireno(2,3-c)(1)benzazocin-8-yl)methyl hydrogen carbonimidateYield 74.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

A solution of 4-formyl-6,9-dihydroxy-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-trien-8-ylmethyl carbamate (140 mg) in methanol (10 ml) 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 in vacuo to give 6,9-dihydroxy-4-hydroxymethyl-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-trien-8-ylmethyl carbamate (105 mg).

Workup

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

Sources & evidence

ORD record
ord-15254d281f4145bab484d76c6e9261dd
Source dataset
uspto-grants-1989_08
Patent number
US04861774

Reaction notes

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