Methanol → HCID 69064616, compound

HRID 1784347Notes

Reaction equation

HRID 1784347 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:13][CH2:12][C@@H:11]3[CH2:14][CH2:15][CH2:16][N:10]3[C:9](=[O:17])[C:8]=2[CH:18]=1)([O-])=O.CO.[H][H]>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[O:13][CH2:12][C@@H:11]3[CH2:14][CH2:15][CH2:16][N:10]3[C:9](=[O:17])[C:8]=2[CH:18]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 69064249HCID 69064249, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 69064616HCID 69064616, compoundYield 93.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of (S)-7-nitro-2,3,11,11a-tetrahydro-1H,5H-pyrrolo[2,1-c][1,4]benzoxazepine-5-one (7.4 g), prepared as described in Example 3L, in ethanol (100 ml) and methanol (50 ml) was hydrogenated over 10% palladium on activated carbon under 2 bar hydrogen, until the uptake of hydrogen ceased. The mixture was filtered to remove the catalyst and evaporated to dryness in vacuo. The crude product was passed through a short silica column (eluting with 10% methanol in dichloromethane) to give the title product (6.1 g). EIMS: m/z=219 [M+H]+

Workup

  1. filtrationThe mixture was filtered
  2. customto remove the catalyst
  3. customevaporated to dryness in vacuo
  4. washThe crude product was passed through a short silica column (eluting with 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-9e4e3e7114bc4854bd74b57e4f8595b1
Source dataset
uspto-grants-2009_03
Patent number
US07504390B2

Reaction notes

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