Methanol → HCID 67319442, compound

HRID 2047461Notes

Reaction equation

HRID 2047461 reaction equation
CO.[F:3][C:4]1[CH:5]=[CH:6][C:7]([C@@H:10]2[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:12][C@H:11]2[C:22]([O:24]C)=[O:23])=[N:8][CH:9]=1.[OH-].[Na+]>O>[C:18]([O:17][C:15]([N:13]1[CH2:14][C@@H:10]([C:7]2[CH:6]=[CH:5][C:4]([F:3])=[CH:9][N:8]=2)[C@H:11]([C:22]([OH:24])=[O:23])[CH2:12]1)=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 86655662HCID 86655662, compound

Product 1

HCID 67319442HCID 67319442, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a methanol solution of the compound (2.8 g) obtained in step 7 was added a solution of sodium hydroxide (0.7 g) in water (30 mL), and the mixture was stirred at room temperature for 3 hr. The mixture was concentrated under reduced pressure, diluted with water, and washed with ethyl acetate. The aqueous layer was acidified (pH 5) with acetic acid, extracted with dichloromethane, dried and concentrated under reduced pressure to give (3S,4S)-1-(tert-butoxycarbonyl)-4-(5-fluoropyridin-2-yl)pyrrolidine-3-carboxylic acid (2.3 g, 85%) as a white oil.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additiondiluted with water
  3. washwashed with ethyl acetate
  4. extractionextracted with dichloromethane
  5. customdried
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c3ca49200974481789ea162a31010ff0
Source dataset
uspto-grants-2013_11
Patent number
US08592454B2

Reaction notes

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