Sodium Hydroxide → HCID 52271561, compound

HRID 2282887Notes

Reaction equation

HRID 2282887 reaction equation
[F:1][C@@:2]1([C:14]([O:16]C)=[O:15])[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.[OH-].[Na+]>CO>[C:10]([O:9][C:7]([N:4]1[CH2:5][CH2:6][C@@:2]([F:1])([C:14]([OH:16])=[O:15])[CH2:3]1)=[O:8])([CH3:13])([CH3:11])[CH3:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86685755Methyl (S)-1-Boc-3-fluoropyrrolidine-3-carboxylate

Product 1

HCID 52271561HCID 52271561, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of #167 (238 mg, 0.963 mmol, 1 eq.) dissolved in methanol (2.6 mL) was added an aqueous solution of sodium hydroxide (2.5 M, 0.88 mL) and the reaction was stirred at room temperature for 3 hours. The reaction was then quenched with 10% aqueous citric acid (5 mL) and ethyl acetate (100 mL) was added, and the layers were separated. The organic layer was washed with 10% citric acid, water, and brine, then dried over sodium sulfate, filtered and concentrated in vacuo to afford #169 as a white solid (221 mg, 99%). 1H NMR (400 MHz, CDCl3), δ 3.96-3.69 (m, 3H), 3.59 (m, 1H), 2.59-2.33 (m, 2H), 1.51 (s, 9H). LC-MS (Protocol Q1): m/z 232.1 [M−H+], retention time=0.67 minutes. Chiral HPLC retention time: 3.95 min (purity=98%) (Column: Chiralpak AD-H, 4.6 mm×25 cm, mobile phase 5-60% CO2/Methanol, flow rate 3.0 mL/min); Optical rotation: [α]D25 −3.6 (c=0.55, MeOH)

Workup

  1. customThe reaction was then quenched with 10% aqueous citric acid (5 mL) and ethyl acetate (100 mL)
  2. additionwas added
  3. customthe layers were separated
  4. washThe organic layer was washed with 10% citric acid, water, and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dde25e816ea54e35ad79c68093388317
Source dataset
uspto-grants-2015_09
Patent number
US09138486B2

Reaction notes

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