Sodium Methoxide → (+)-trans-1-(3,4-Dichlorobenzamido)-2-hydroxy-7-(pyrrolidinoformamido)tetraline

HRID 1937364Notes

Reaction equation

HRID 1937364 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][C:32]=1[Cl:33])[C:5]([NH:7][C@@H:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([NH:18][C:19]([N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[O:20])[CH:16]=2)[CH2:11][CH2:10][C@H:9]1[O:26]C(=O)C)=[O:6].C[O-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][C:32]=1[Cl:33])[C:5]([NH:7][C@@H:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([NH:18][C:19]([N:21]3[CH2:22][CH2:23][CH2:24][CH2:25]3)=[O:20])[CH:16]=2)[CH2:11][CH2:10][C@H:9]1[OH:26])=[O:6]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 21338527(+)-trans-1-(3,4-Dichlorobenzamido)-2-acetoxy-7-(pyrrolidinoformamido)tetraline

Product 1

HCID 21338529(+)-trans-1-(3,4-Dichlorobenzamido)-2-hydroxy-7-(pyrrolidinoformamido)tetraline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 116 (0.27 g) in MeOH (10 mL) was treated with 0.135 M sodium methoxide (4.9 mL) in MeOH. After 4 h, the solvent was evaporated, the residue was suspended in H2O, and the solid was collected by filtration. The solid was crystallized from EtOAc-ether to give a tan powder, m.p. 206-208° C.

Workup

  1. customthe solvent was evaporated
  2. filtrationthe solid was collected by filtration
  3. customThe solid was crystallized from EtOAc-ether
  4. customto give a tan powder, m.p. 206-208° C.

Sources & evidence

ORD record
ord-00a7c8bd925e41b2bbb193d901cc3190
Source dataset
uspto-grants-2002_05
Patent number
US06395735B2

Reaction notes

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