Water → HCID 22406830, compound

HRID 440520Notes

Reaction equation

HRID 440520 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:25]2[C:34]3[C:29](=[CH:30][C:31]([F:36])=[C:32]([OH:35])[CH:33]=3)[CH2:28][CH2:27][N:26]2[CH3:37])[CH2:24][CH2:23][CH2:22]1.C(N(CC)CC)C.O>ClCCl>[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1([CH:25]2[C:34]3[C:29](=[CH:30][C:31]([F:36])=[C:32]([O:35][C:1](=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH:33]=3)[CH2:28][CH2:27][N:26]2[CH3:37])[CH2:24][CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 66982Decanoyl chlorideHCID 22406846HCID 22406846, compound

Product 1

HCID 22406830HCID 22406830, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Decanoyl chloride (0.66 g) in dichloromethane (5 ml) was added to a stirring mixture of (+)-1-[1-(2-chlorophenyl)cyclobutyl]-6-fluoro-7-hydroxy-2-methyl-1,2,3,4-tetrahydroisoquinoline hydrobromide (1.5 g, prepared in a similar manner to that described in Example 64), triethylamine (1.06 g) and dichloromethane (25 ml). The mixture was stirred at ambient temperature for 20 minutes, then water (20 ml) was added and stirring continued for 1 hour. The organic layer was washed with saturated aqueous sodium bicarbonate solution, water and brine, then dried over magnesium sulphate, filtered and concentrated in vacuo to yield (-)-1-[1-(2-chlorophenyl)cyclobutyl]-7-decanoyloxy-6-fluoro-2-methyl-1,2,3,4-tetrahydroisoquinoline (1.31 g). This had a specific optical rotation αD of -5.59°.

Workup

  1. customprepared in a similar manner to that
  2. stirringstirring
  3. waitcontinued for 1 hour
  4. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution, water and brine
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-58018fa0779342c4b5ca7e782b0bbfbd
Source dataset
uspto-grants-1996_05
Patent number
US05519034

Reaction notes

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