Dichloromethane → 6-Chloro-7-ethoxy-4-methyl-1,2,3,4-tetrahydro-2,4a,5-triaza-fluorene

HRID 1272097Notes

Reaction equation

HRID 1272097 reaction equation
C(OC([N:8]1[CH2:20][C@@H:19]([CH3:21])[N:18]2[C:10](=[CH:11][C:12]3[C:17]2=[N:16][C:15]([Cl:22])=[C:14]([O:23][CH2:24][CH3:25])[CH:13]=3)[CH2:9]1)=O)(C)(C)C.ClCCl>>[Cl:22][C:15]1[N:16]=[C:17]2[C:12](=[CH:13][C:14]=1[O:23][CH2:24][CH3:25])[CH:11]=[C:10]1[N:18]2[CH:19]([CH3:21])[CH2:20][NH:8][CH2:9]1

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 86596339(R)-6-chloro-7-ethoxy-4-methyl-3,4-dihydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

Product 1

HCID 184559876-Chloro-7-ethoxy-4-methyl-1,2,3,4-tetrahydro-2,4a,5-triaza-fluoreneYield 89.5%

Procedure

To a solution of 0.12 g (0.33 mmol) (R)-6-chloro-7-ethoxy-4-methyl-3,4-dihydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester in 3 mL dichloromethane 1.5 mL (2.23 g, 19.6 mmol) trifluoroacetic acid was added. After 1 h the volatile components were evaporated and the residue was purified by column chromatography on silica gel (0.030–0.063 mm) with dichloromethane:methanol:ammonia (19:1:0.1) as eluant to give the desired compound as a light yellow solid (89.5%)

Workup

  1. customAfter 1 h the volatile components were evaporated
  2. customthe residue was purified by column chromatography on silica gel (0.030–0.063 mm) with dichloromethane:methanol:ammonia (19:1:0.1) as eluant

Sources & evidence

ORD record
ord-bd9d349425ca4232a9bdf85f04e29ee0
Source dataset
uspto-grants-2007_04
Patent number
US07208494B2

Reaction notes

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