1,2,3,4-Tetrahydro-7-phenylmethoxy-4-methycyclopent[b]indole-2-methanol → 1,2,3,4-Tetrahydro-2-hydroxymethyl-4-methylcyclopent[b]indol-7-ol

HRID 2226934Notes

Reaction equation

HRID 2226934 reaction equation
C1(C[O:8][C:9]2[CH:17]=[CH:16][C:15]3[N:14]([CH3:18])[C:13]4[CH2:19][CH:20]([CH2:22][OH:23])[CH2:21][C:12]=4[C:11]=3[CH:10]=2)C=CC=CC=1.[H][H]>C(O)C.[Pd]>[OH:23][CH2:22][CH:20]1[CH2:19][C:13]2[N:14]([CH3:18])[C:15]3[CH:16]=[CH:17][C:9]([OH:8])=[CH:10][C:11]=3[C:12]=2[CH2:21]1

Participants

5

Reactant 2

HCID 189639931,2,3,4-Tetrahydro-7-phenylmethoxy-4-methycyclopent[b]indole-2-methanolHCID 178418361HCID 178418361, compound

Product 1

HCID 189639901,2,3,4-Tetrahydro-2-hydroxymethyl-4-methylcyclopent[b]indol-7-olYield 68.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

To a suspension of 10% Pd/C (1.2 g) in 50 ml of ethanol was added a solution of 1,2,3,4-tetrahydro-7-phenylmethoxy-4-methylcyclopent[b]indole-2-methanol (8.4 g, 0.027 mole) in 200 ml of ethanol in a Parr hydrogenation bottle. After shaking at 50° C., under 50 psi hydrogen for two hours, the mixture was cooled, filtered, and then concentrated to a dark oil. The oil was eluted on a silica gel column with ethyl acetate/dichloromethane (1:2) via HPLC. The desired fractions were combined and then concentrated to a light yellow solid. The material was triturated with ether and dried to give 4.0 g (66%) of the product as an off-white solid, m.p. 153°-4° C.

Workup

  1. temperaturethe mixture was cooled
  2. filtrationfiltered
  3. concentrationconcentrated to a dark oil
  4. washThe oil was eluted on a silica gel column with ethyl acetate/dichloromethane (1:2) via HPLC
  5. concentrationconcentrated to a light yellow solid
  6. customThe material was triturated with ether
  7. customdried

Sources & evidence

ORD record
ord-10bde5ac28a043e6aeeb580eaa6bb9a2
Source dataset
uspto-grants-1994_09
Patent number
US05350762

Reaction notes

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