p-Toluenesulfonic acid → (4R,9aR)-6-(2-hydroxy-ethoxymethyl)-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

HRID 11942Notes

Reaction equation

HRID 11942 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:20][C@@H:19]([CH3:21])[N:18]2[C@H:10]([CH2:11][C:12]3[C:17]2=[N:16][C:15]([CH2:22][O:23][CH2:24][CH2:25][O:26]C2CCCCO2)=[CH:14][CH:13]=3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[C:1]([O:5][C:6]([N:8]1[CH2:20][C@@H:19]([CH3:21])[N:18]2[C@H:10]([CH2:11][C:12]3[C:17]2=[N:16][C:15]([CH2:22][O:23][CH2:24][CH2:25][OH:26])=[CH:14][CH:13]=3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 69557443(4R,9aR)-4-Methyl-6-[2-(tetrahydro-pyran-2-yloxy)-ethoxymethyl]-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

Product 1

HCID 69557393(4R,9aR)-6-(2-hydroxy-ethoxymethyl)-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl esterYield 71.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the solution of 0.16 g (0.36 mmol) (4R,9aR)-4-methyl-6-[2-(tetrahydro-pyran-2-yloxy)-ethoxymethyl]-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester in 3 ml methanol was added 0.136 g (0.71 mmol) para-toluenesulphonic acid. After 30 min, the solvent was removed on a rotary evaporator and the residue was chromatographed on silica gel (0.032–0.063 mm) with dichloromethane:methanol:ammonia (19:1:0.1) as eluant to afford the desired compound as a light yellow oil (71.6%).

Workup

  1. customthe solvent was removed on a rotary evaporator
  2. customthe residue was chromatographed on silica gel (0.032–0.063 mm) with dichloromethane:methanol:ammonia (19:1:0.1) as eluant

Sources & evidence

ORD record
ord-3f70284bb0ad4e6594155aded5cc3234
Source dataset
uspto-grants-2006_08
Patent number
US07098337B2

Reaction notes

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