Sodium Hydroxide → HCID 70900790, compound

HRID 1852941Notes

Reaction equation

HRID 1852941 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([N:10]2[CH2:14][CH2:13][CH:12]([C:15]([O:17]C)=[O:16])[CH2:11]2)[CH:7]=[CH:8][CH:9]=1>C1COCC1.CO>[Br:3][C:4]1[CH:5]=[C:6]([N:10]2[CH2:14][CH2:13][CH:12]([C:15]([OH:17])=[O:16])[CH2:11]2)[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53403226HCID 53403226, compound

Product 1

HCID 70900790HCID 70900790, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

1M NaOH aq. (2 mL) was added to a solution of methyl 1-(3-bromophenyl)pyrrolidine-3-carboxylate in THF-MeOH (1 mL-1 mL). After stirring the mixture at room temperature for 13 hours, the mixture was concentrated. The residue was diluted with 1M NaOH aq. and washed with ether. The aqueous layer was acidified with 1M HCl aq. and extracted with DCM (3×). The combined organic layer was dried over anhydrous Na2SO4 and concentrated to afford desired product (293 mg, 83.9%) as yellow solid.

Workup

  1. concentrationthe mixture was concentrated
  2. additionThe residue was diluted with 1M NaOH aq.
  3. washwashed with ether
  4. extractionextracted with DCM (3×)
  5. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e1b8b3a75393483c93dbd5f9aed5a3ee
Source dataset
uspto-grants-2015_02
Patent number
US08962619B2

Reaction notes

Loading…