Water → 4-pyrrolidin-1-ylnaphthalene-1-carboxylic Acid

HRID 916318Notes

Reaction equation

HRID 916318 reaction equation
C([O:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:8][CH:7]=1)=[O:5])C.[Li+].[OH-].O.C1COCC1>C(OCC)(=O)C>[N:16]1([C:9]2[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:6]([C:4]([OH:5])=[O:3])=[CH:7][CH:8]=2)[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 962Water2×HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 115072934-Pyrrolidin-1-ylnaphthalene-1-carboxylic acid ethyl ester

Product 1

HCID 115649704-pyrrolidin-1-ylnaphthalene-1-carboxylic AcidYield 68%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

154BG19 (30 mg, 0.11 mmol) was transferred to a Pyrex tube and LiOH×H2O (14 mg, 0.33 mmol) was added, followed by H2O (0.18 mL) and THF (0.37 mL). The tube was capped and the reaction tube was exposed to microwave irradiation (160° C., 5 min). The reaction mixture was transferred to a separation funnel with ethyl acetate and washed with 2 M NaOH. The aqueous phase was acidified with 2 M HCl and extracted with ethyl acetate. The organic phases were collected, dried over Na2SO4, filtered and concentrated to yield 18 mg (68%) of the title compound.

Workup

  1. additionwas added
  2. customThe tube was capped
  3. customthe reaction tube was exposed to microwave irradiation (160° C., 5 min)
  4. washwashed with 2 M NaOH
  5. extractionextracted with ethyl acetate
  6. customThe organic phases were collected
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-3ff5fac29ee44c4694f2929a27271f01
Source dataset
uspto-grants-2007_09
Patent number
US07268232B2

Reaction notes

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