Dichloromethane → HCID 22406761, compound

HRID 440521Notes

Reaction equation

HRID 440521 reaction equation
[C:1](Cl)(=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].Br.[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1([CH:24]2[C:33]3[C:28](=[CH:29][C:30]([F:35])=[C:31]([OH:34])[CH:32]=3)[CH2:27][CH2:26][N:25]2[CH3:36])[CH2:23][CH2:22]1.ClCCl.C(N(CC)CC)C>O>[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1([CH:24]2[C:33]3[C:28](=[CH:29][C:30]([F:35])=[C:31]([O:34][C:1](=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH:32]=3)[CH2:27][CH2:26][N:25]2[CH3:36])[CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 66982Decanoyl chlorideHCID 22406801HCID 22406801, compound

Product 1

HCID 22406761HCID 22406761, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Decanoyl chloride (0.61 g) was added to a stirring suspension of (+)-1- [1-(2-chlorophenyl)cyclopropyl]-6-fluoro-7-hydroxy-2-methyl-1,2,3,4-tetrahydroisoquinoline hydrobromide (1 g, prepared in a similar manner to that described in Example 62) and dichloromethane (25 ml). Triethylamine (1.35 ml) was added and the stirring was maintained for 1.5 hours. Water was then added, and the organic layer washed with 2N aqueous sodium hydroxide solution, then water and dried over potassium carbonate. The solvent was removed in vacuo and the residual oil was purified by liquid chromatography using petroleum ether (b.p. 40°-60° C.) as impurity eluant, then 5% ether in petroleum ether (b.p. 40°-60° C.) as product eluant. The solvent was removed in vacuo to yield (+)-1-[1-(2-chlorophenyl)cyclopropyl]-7-decanoyloxy-6-fluoro-2-methyl-1,2,3,4-tetrahydroisoquinoline (0.85 g) which had a specific optical rotation αD of +10.6°.

Workup

  1. customprepared in a similar manner to that
  2. temperaturethe stirring was maintained for 1.5 hours
  3. washthe organic layer washed with 2N aqueous sodium hydroxide solution
  4. dry with materialwater and dried over potassium carbonate
  5. customThe solvent was removed in vacuo
  6. customthe residual oil was purified by liquid chromatography
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-56e60a2475a640779ee95dac420d7db0
Source dataset
uspto-grants-1996_05
Patent number
US05519034

Reaction notes

Loading…