7a-(3-benzyloxy-5-pyridinyl)-hexahydro-1H-pyrrolizine → 7a-(3-hydroxy-5-pyridinyl)-hexahydro-1H-pyrrolizine

HRID 3311

Reaction equation

HRID 3311 reaction equation
C([O:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13]([C:15]23[CH2:22][CH2:21][CH2:20][N:19]2[CH2:18][CH2:17][CH2:16]3)[CH:14]=1)C1C=CC=CC=1>CO.[Pt]>[OH:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13]([C:15]23[CH2:16][CH2:17][CH2:18][N:19]2[CH2:20][CH2:21][CH2:22]3)[CH:14]=1

Participants

4

Reactant 1

HCID 189347547a-(3-benzyloxy-5-pyridinyl)-hexahydro-1H-pyrrolizine

Product 1

HCID 189347307a-(3-hydroxy-5-pyridinyl)-hexahydro-1H-pyrrolizineYield 63.4%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

7a-(3-Benzyloxy-5-pyridinyl)-hexahydro-1H-pyrrolizine (260 mg, 0.88 mmol, from step 16b) was dissolved in methanol (9 mL), 10% Pt/C (35 mg) was added, and the mixture stirred under 1 arm of H2 for 16 hours. The catalyst was removed, the filtrate was concentrated, and the residue was chromatographed (silica gel; CHCl3 /MeOH/0.5 % NH4OH, 90:10:0 to 90:10:0.5) to afford the title compound as a white solid (114 mg, 63%). 1H NMR D2O, 300 MHz) δ2.07-2.40 (m, 6H), 2.49-2.58 (m, 2H), 3.26-3.34 (m, 2H), 3.71-3.80 (m, 2H), 7.00 (dd, J=2.4, 2.0 Hz, 1H), 7.80 (d, J=2.0 Hz, 1H), 7.85 (d, J=2.4 Hz, 1H): MS (CI/NH3) m/z: 205 (M+H)+.

Workup

  1. customThe catalyst was removed
  2. concentrationthe filtrate was concentrated
  3. customthe residue was chromatographed (silica gel; CHCl3 /MeOH/0.5 % NH4OH, 90:10:0 to 90:10:0.5)

Sources & evidence

ORD record
ord-94eabea82a724e06b470656c1d0fc4ec
Source dataset
uspto-grants-1998_03
Patent number
US05733912

Linked notes

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