6-Benzyloxy-1,1-dimethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole → HCID 19935696, compound

HRID 484253Notes

Reaction equation

HRID 484253 reaction equation
[CH3:1][C:2]1([CH3:23])[C:7]2[NH:8][C:9]3[C:14]([C:6]=2[CH2:5][CH2:4][O:3]1)=[CH:13][C:12]([O:15]CC1C=CC=CC=1)=[CH:11][CH:10]=3>[Pd].C(O)C>[CH3:1][C:2]1([CH3:23])[C:7]2[NH:8][C:9]3[C:14]([C:6]=2[CH2:5][CH2:4][O:3]1)=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=3

Participants

4

Reactant 1

HCID 199357106-Benzyloxy-1,1-dimethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole

Product 1

HCID 19935696HCID 19935696, compoundYield 115.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture consisting of 10% Pd/c on charcoal (0.7 g), ethanol (150 mL) and 1,3,4,9-tetrahydro-1,1-dimethyl-6-(phenylmethoxy)pyrano[3,4-b]indole (4.2 g, 0.014 mol) of Step A, is hydrogenated at 30 psi for 18 hours. The reaction mixture is filtered and concentrated to give 3.5 g product which is used in the next reaction without further purification.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-e4f63fbae7a448d099dd3949836087c6
Source dataset
uspto-grants-1993_07
Patent number
US05229516

Reaction notes

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