Tetrahydrofuran → HCID 66890305, compound

HRID 1671372Notes

Reaction equation

HRID 1671372 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([CH:13]=[O:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:15]1COC[CH2:16]1.C([Mg]Br)C>>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([CH:13]([OH:14])[CH2:15][CH3:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 1514343(S)-tert-butyl 3-formylpyrrolidine-1-carboxylateHCID 178418443HCID 178418443, compound

Product 1

HCID 66890305HCID 66890305, compound

Conditions

Temperature
-78 °C

Procedure

(S)-3-Formylpyrrolidine-1-carboxylic acid t-butyl ester (1 g, 5 mmol) and THF (10 mL, 100 mmol) were combined under nitrogen, and the resulting solution cooled to −78° C. 1.0 M of Ethyl magnesium bromide in THF (7.5 mL, 7.5 mmol) was added dropwise over 10 minutes. The mixture was allowed to warm to room temperature slowly overnight. The reaction was then quenched by the dropwise addition of saturated aqueous NH4Cl (30 mL). The resulting mixture was extracted with EtOAc (2×30 mL), and the combined organic layers were washed with saturated aqueous NaHCO3 (1×30 mL) and saturated aqueous NaCl (1×30 mL), then dried over anhydrous MgSO4, filtered, and concentrated in vacuo to yield (S)-3-(1-hydroxypropyl)pyrrolidine-1-carboxylic acid t-butyl ester.

Workup

  1. temperatureto warm to room temperature slowly overnight
  2. customThe reaction was then quenched by the dropwise addition of saturated aqueous NH4Cl (30 mL)
  3. extractionThe resulting mixture was extracted with EtOAc (2×30 mL)
  4. washthe combined organic layers were washed with saturated aqueous NaHCO3 (1×30 mL) and saturated aqueous NaCl (1×30 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3e053561b6cb4249b88d38832493c17b
Source dataset
uspto-grants-2011_08
Patent number
US07994209B2

Reaction notes

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