Lithium Hydroxide → lithium (3S)-1-(tert-butoxycarbonyl)-3-fluoropyrrolidine-3-carboxylate

HRID 74800Notes

Reaction equation

HRID 74800 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@:10]([F:16])([C:13]([OH:15])=[O:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+:18].O1CCCC1>CO.O>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@:10]([F:16])([C:13]([O-:15])=[O:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3].[Li+:18]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 52271561HCID 52271561, compound

Product 1

HCID 86685757lithium (3S)-1-(tert-butoxycarbonyl)-3-fluoropyrrolidine-3-carboxylateYield 100.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of #169 (75 mg, 0.32 mmol, 1 eq.) in methanol (0.3 mL) was added a solution of lithium hydroxide (13.8 mg, 0.572 mmol, 1.8 eq.) in water (0.4 mL). Next, tetrahydrofuran (0.45 mL) was added and the reaction was stirred at 45° C. for 18 hours. The reaction was concentrated in vacuo and the material was azeotroped (3×) with toluene (4 mL) to obtain #171 (77 mg, 100%) as a white solid, which was used in the next step without further purification.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe material was azeotroped (3×) with toluene (4 mL)

Sources & evidence

ORD record
ord-9f20040a8e444b6ba308da3fe089410c
Source dataset
uspto-grants-2014_09
Patent number
US08828401B2

Reaction notes

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