Dichloromethane → HCID 42641991, compound

HRID 2382178Notes

Reaction equation

HRID 2382178 reaction equation
[CH3:1][C@@H:2]1[CH2:7][N:6]([CH:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][CH2:11][CH2:10][CH2:9]2)[CH2:5][CH2:4][N:3]1[CH2:19][C:20]([O:22]C)=[O:21].O.[OH-].[Li+].C(Cl)Cl.C(Cl)Cl.CO>CO.C1COCC1.O>[CH3:1][C@@H:2]1[CH2:7][N:6]([CH:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][CH2:11][CH2:10][CH2:9]2)[CH2:5][CH2:4][N:3]1[CH2:19][C:20]([OH:22])=[O:21]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 168937Lithium hydroxide, monohydrateHCID 21226129Dichloromethane methanolHCID 68771915HCID 68771915, compound

Product 1

HCID 42641991HCID 42641991, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To methyl 2-((R)-2-methyl-4-(6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-yl)piperazin-1-yl)acetate (420 mg, 1.327 mμmol) in 14 mL of MeOH/THF/H2O (3:3:1) was added lithium hydroxide monohydrate (195 mg, 4.645 mmol). After stirring at rt for 3 h when HPLC-MS showed complete conversion, the solvent was evaporated to dryness under high vacuum. The residue was redissolved in water and the solution was adjusted to PH=4 with 2 N HCl, extracted with DCM, dried over Na2SO4, filtered and evaporated to dryness. Column chromatography (SiO2, DCM to DCM/MeOH=100:10 to 100:20 to 100:30) gave 2-((R)-2-methyl-4-(6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-yl)piperazin-1-yl)acetic acid (360 mg, 89.7% yield) as a white solid. MS (ESI, pos. ion) m/z: 303.2 (M+1).

Workup

  1. customthe solvent was evaporated to dryness under high vacuum
  2. dissolutionThe residue was redissolved in water
  3. extractionextracted with DCM
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-2c01b097ccb348e9b85a86199114ef0d
Source dataset
uspto-grants-2012_09
Patent number
US08258306B2

Reaction notes

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