Sodium Hydroxide → HCID 52271559, compound

HRID 2282886Notes

Reaction equation

HRID 2282886 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 86685754Methyl (R)-1-Boc-3-fluoropyrrolidine-3-carboxylate

Product 1

HCID 52271559HCID 52271559, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of #166 (272 mg, 1.10 mmol, 1 eq.) dissolved in methanol (2.96 mL) was added an aqueous solution of sodium hydroxide (2.5 M, 0.88 mL) and the reaction was stirred at room temperature for 3.5 hours. The reaction was quenched with 10% aqueous citric acid (5 mL), ethyl acetate (100 mL) was added, and the layers separated. The organic layer was washed with 10% citric acid, water, and brine, dried over sodium sulfate, filtered and concentrated in vacuo to afford #168 as a white solid. (253 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: 3.39 min (purity=99%). (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 4.8 (c=0.52, MeOH)

Workup

  1. customThe reaction was quenched with 10% aqueous citric acid (5 mL), ethyl acetate (100 mL)
  2. additionwas added
  3. customthe layers 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-a5afa24983b142b5adebc1e028b93230
Source dataset
uspto-grants-2015_09
Patent number
US09138486B2

Reaction notes

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