Oxygen → HCID 10104277, compound

HRID 1492692Notes

Reaction equation

HRID 1492692 reaction equation
O=O.[CH:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[C:6]1[CH:15]=[C:14]([CH2:16][OH:17])[CH2:13][CH2:12][N:7]12>C1(C)C=CC=CC=1>[CH:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[C:6]1[CH2:15][C@H:14]([CH2:16][OH:17])[CH2:13][CH2:12][N:7]12

Participants

4

Reactant 2

HCID 977OxygenHCID 10878148HCID 10878148, compound

Product 1

HCID 10104277HCID 10104277, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The glass attachment of a 30 ml autoclave is charged in a glove box (oxygen content <1 ppm) with 0.20 g (1.0 mmol) of 6,7-dihydropyrido[1,2-a]indole-8-methanol, 8 ml of toluene and 2 ml of the above-mentioned catalyst solution. The hydrogenation is carried out at 80° C., an initial pressure of 60 bar of H2 and while stirring vigorously. After a hydrogenation time of 18 hours, the conversion is 99.9% according to GC. The pale yellow hydrogenation solution is evaporated. The residue is dissolved in diethyl ether and the solution is allowed to flow through a 5 g silica gel column in order to separate the catalyst. Rinsing of the column with diethyl ether, evaporation of the eluate and drying of the pale brown crystalline residue, yields 0.20 g (100%) of (R)-6,7,8,9-tetrahydropyrido[1,2-a]indole-8-methanol; GC 100 area %, 93.7% e.e.

Workup

  1. customis carried out at 80° C.
  2. customAfter a hydrogenation time of 18 hours
  3. customThe pale yellow hydrogenation solution is evaporated
  4. dissolutionThe residue is dissolved in diethyl ether
  5. customto separate the catalyst
  6. washRinsing of the column with diethyl ether, evaporation of the eluate and
  7. customdrying of the pale brown crystalline residue

Sources & evidence

ORD record
ord-1a60b9ff1bbf45f8a975e30004d2fbc3
Source dataset
uspto-grants-1994_12
Patent number
US05374727

Reaction notes

Loading…