HCID 67931169, compound → HCID 45261289, compound

HRID 982113Notes

Reaction equation

HRID 982113 reaction equation
[ClH:1].[NH2:2][CH2:3][C@H:4]1[C:9]2[CH:10]=[CH:11][C:12]([O:22][CH3:23])=[C:13]([O:14]CC3C=CC=CC=3)[C:8]=2[CH2:7][C@@H:6]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[O:5]1>CO.[Pd].C(OCC)(=O)C>[ClH:1].[NH2:2][CH2:3][C@H:4]1[C:9]2[CH:10]=[CH:11][C:12]([O:22][CH3:23])=[C:13]([OH:14])[C:8]=2[CH2:7][C@@H:6]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[O:5]1

Participants

5

Reactant 1

HCID 67931169HCID 67931169, compound

Product 1

HCID 45261289HCID 45261289, compoundYield 66.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 940 mg (2.28 mmol) of [1R,3S] 1-aminomethyl-5-benzyloxy-3,4-dihydro--6-methoxy-3-phenyl-1H-2-benzopyran hydrochloride, from Step 9, in 500 mL of methanol was treated with 500 mg of 10% palladium on carbon and the resultant mixture was shaken under a hydrogen atmosphere for 24 h. The reaction mixture was diluted with ethyl acetate and filtered through Celite filter aid. The filtrate was concentrated in vacuo to give an off-white solid which was crystallized from methanol/methylene chloride/ether to give 488 mg (66% yield) of the title compound, m.p. 234° C.; MS DCl-NH3M/Z: 286 (M+H)+. Analysis calculated for C17H20ClNO3 +0.25 CH2Cl2 : C, 60.40; H, 6.02; N, 4.08. Found: C, 60.07; H, 5.97; N, 4.03.

Workup

  1. filtrationfiltered through Celite
  2. filtrationfilter aid
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto give an off-white solid which
  5. customwas crystallized from methanol/methylene chloride/ether

Sources & evidence

ORD record
ord-92894d85c44d4295a818dde6c0050d93
Source dataset
uspto-grants-1991_02
Patent number
US04994486

Reaction notes

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