Tetrahydrofuran → (S)-3-(1-Hydroxyprop-2-ynyl)pyrrolidine-1-carboxylic Acid t-Butyl Ester

HRID 588015Notes

Reaction equation

HRID 588015 reaction equation
[C:1]([Mg]Br)#[CH:2].C1COCC1.[C:10]([O:14][C:15]([N:17]1[CH2:21][CH2:20][C@H:19]([CH:22]=[O:23])[CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11]>>[C:10]([O:14][C:15]([N:17]1[CH2:21][CH2:20][C@H:19]([CH:22]([OH:23])[C:1]#[CH:2])[CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11]

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 1514343(S)-tert-butyl 3-formylpyrrolidine-1-carboxylateHCID 178418486HCID 178418486, compound

Product 1

HCID 58104606(S)-3-(1-Hydroxyprop-2-ynyl)pyrrolidine-1-carboxylic Acid t-Butyl Ester

Procedure

0.5 M Ethynylmagnesium bromide in THF (6.3 mL, 3140 μmol) was added dropwise over 5 minutes to a stirred solution of (S)-3-formylpyrrolidine-1-carboxylic acid t-butyl ester (0.5 g, 2 mmol) in THF (5 mL, 60 mmol) at 0° C. The mixture was allowed to warm to room temperature. After 4 hours, the reaction was quenched with the addition of saturated aqueous NH4Cl (10 mL) and extracted with EtOAc (2×10 mL). The organic layers were combined, dried over MgSO4, filtered, and concentrated in vacuo.

Workup

  1. customthe reaction was quenched with the addition of saturated aqueous NH4Cl (10 mL)
  2. extractionextracted with EtOAc (2×10 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c2d8bd53358048e3bd1d591a14d3898f
Source dataset
uspto-grants-2016_01
Patent number
US09227933B2

Reaction notes

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