HCID 22813385, compound → HCID 22813387, compound

HRID 1732589Notes

Reaction equation

HRID 1732589 reaction equation
[CH:1]1[C:9]2[C@H:10]3[O:15][CH2:14][CH2:13][NH:12][C@@H:11]3[CH2:16][C:7]3[C:8]=2[C:4]([NH:5][CH:6]=3)=[CH:3][CH:2]=1>[Pd].C(O)C>[CH2:9]([N:12]1[C@@H:11]2[CH2:16][C:7]3[C:8]4[C:4]([NH:5][CH:6]=3)=[CH:3][CH:2]=[CH:1][C:9]=4[C@H:10]2[O:15][CH2:14][CH2:13]1)[CH2:1][CH2:2][CH3:3]

Participants

4

Reactant 1

HCID 22813385HCID 22813385, compound

Product 1

HCID 22813387HCID 22813387, compoundYield 56.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of trans-4,6,6a,8,9,10a-hexahydro-7H-indolo-[3,4 gh]-[1,4]-benzoxazine (700 mg; 0.0032 m), Pd/c (10%, 700 mg) and butrylaldehyde (500 mg, 0.006 m) in abs. ethanol (75 ml) is hydrogenated at room temperature for 8 hours. The catalyst is filtered, and the solvent is removed under reduced pressure (20 mm). The resulting oil is chromatographed (silica, chloroform, saturated with aqueous ammonia). The solid is recrystallized from hexane to yield 250 mg of trans-4,6,6a,8,9,10a-hexahydro-7-n-butyl-7H-indolo-[3,4 gh]-[1,4]-benzoxazine; m.p. softens 29°-130°, m.p. 134°-140°.

Workup

  1. filtrationThe catalyst is filtered
  2. customthe solvent is removed under reduced pressure (20 mm)
  3. customThe resulting oil is chromatographed (silica, chloroform, saturated with aqueous ammonia)
  4. customThe solid is recrystallized from hexane

Sources & evidence

ORD record
ord-d840c0e5a50f4ca584c625adaafa2eaa
Source dataset
uspto-grants-1980_12
Patent number
US04238486

Reaction notes

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