Chroman-4-ol → HCID 15056495, compound

HRID 654149Notes

Reaction equation

HRID 654149 reaction equation
C(OC([NH:11][CH2:12][C:13]1([CH3:32])[CH:22]=[C:21]([N:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]2=[O:29])[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([C:30]#[N:31])[CH:19]=2)[O:14]1)=O)C1C=CC=CC=1.C(OC(NCC(=O)C)=O)C1C=CC=CC=1.C(C1(C)C(CN)C(=O)C2C(=CC=C(C#N)C=2)O1)(OCC1C=CC=CC=1)=O.O1C2C(=CC=CC=2)C(O)CC1.OCC1(C)C=C(N2C=CC=CC2=O)C2C(=CC=C(C#N)C=2)O1>O1CCOCC1.[Pd].[C]>[NH2:11][CH2:12][C:13]1([CH3:32])[CH:22]=[C:21]([N:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]2=[O:29])[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([C:30]#[N:31])[CH:19]=2)[O:14]1

Participants

8

Reactant 5

HCID 92890Chroman-4-olHCID 15056494HCID 15056494, compoundHCID 19888574HCID 19888574, compoundHCID 22747857Benzyl 2-oxopropylcarbamateHCID 67917265HCID 67917265, compound

Product 1

HCID 15056495HCID 15056495, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 1 g of 2-benzyloxycarbonylaminomethyl-2-methyl-4-(1,2-dihydro-2-oxo-1-pyridyl)-6-cyano3-chromene [obtainable from 1-benzyloxycarbonylamino-2-propanone ("1-CBZ-2-propanone") via 2-CBZ-aminomethyl-2-methyl-6-cyano-4-chromanone, the corresponding 4-chromanol, the corresponding 3-chromene and the corresponding 3,4-epoxide] in 20 ml of dioxane is hydrogenated on 0.5 g of 5% Pd-carbon at 20° C. and 1 bar until the calculated amount of H2 has been absorbed. The mixture is filtered, the solution is evaporated and 2-aminomethyl-2-methyl-4-(1,2-dihydro-2-oxo-1-pyridyl)-6-cyano-3-chromene is obtained.

Workup

  1. custom1 bar until the calculated amount of H2 has been absorbed
  2. filtrationThe mixture is filtered
  3. customthe solution is evaporated

Sources & evidence

ORD record
ord-171cd426d5c744b0a14a731425883ef1
Source dataset
uspto-grants-1992_07
Patent number
US05130322

Reaction notes

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