Hydrochloric Acid → 4-(1-(Benzyloxycarbonyl)pyrrolidin-2-yl)-2-fluorobenzoic acid

HRID 415155Notes

Reaction equation

HRID 415155 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:12]2[CH2:16][CH2:15][CH2:14][N:13]2[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH:5]=[CH:6][C:7]=1[C:8]([O:10]C)=[O:9].O.[OH-].[Li+].Cl>O1CCCC1.O.CO>[CH2:20]([O:19][C:17]([N:13]1[CH2:14][CH2:15][CH2:16][CH:12]1[C:4]1[CH:5]=[CH:6][C:7]([C:8]([OH:10])=[O:9])=[C:2]([F:1])[CH:3]=1)=[O:18])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 66621283Benzyl 2-(3-fluoro-4-(methoxycarbonyl)phenyl)pyrrolidine-1-carboxylate

Product 1

HCID 666213044-(1-(Benzyloxycarbonyl)pyrrolidin-2-yl)-2-fluorobenzoic acidYield 100.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzyl 2-(3-fluoro-4-(methoxycarbonyl)phenyl)pyrrolidine-1-carboxylate (8.7 g, 24.4 mmol) in tetrahydrofuran (90 mL) was added lithium hydroxide monohydrate (2.05 g, 48.8 mmol) in 90 mL of water (90 mL) and methanol (90 mL) was added until a transparent solution formed. This mixture was stirred at ambient temperature for 2 hours and acidified with 2N hydrochloric acid to pH=2. The mixture was concentrated to about 90 mL, diluted with water and left to stand at ambient temperature overnight. The solid was collected by filtration, washed with water and dried to give 4-(1-(benzyloxycarbonyl)pyrrolidin-2-yl)-2-fluorobenzoic acid (8.4 g, yield 98%). LC-MS (ESI) m/z: 344 (M+1)+.

Workup

  1. additionwas added until a transparent solution
  2. customformed
  3. concentrationThe mixture was concentrated to about 90 mL
  4. additiondiluted with water
  5. waitleft
  6. waitto stand at ambient temperature overnight
  7. filtrationThe solid was collected by filtration
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-37400522e0124895bdf32ae92ed4a736
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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