tert-Butyl 2-(2-methoxy-2-oxoethyl)pyrrolidine-1-carboxylate → tert-Butyl 2-(2-hydroxyethyl)pyrrolidine-1-carboxylate

HRID 2167095Notes

Reaction equation

HRID 2167095 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([O:11][C:12]([N:14]1[CH2:18][CH2:17][CH2:16][CH:15]1[CH2:19][C:20](OC)=[O:21])=[O:13])([CH3:10])([CH3:9])[CH3:8]>C1COCC1>[C:7]([O:11][C:12]([N:14]1[CH2:18][CH2:17][CH2:16][CH:15]1[CH2:19][CH2:20][OH:21])=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 13425758tert-Butyl 2-(2-methoxy-2-oxoethyl)pyrrolidine-1-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 13425759tert-Butyl 2-(2-hydroxyethyl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of LAH (0.94 g, 24.69 mmol) in dry THF (100 mL) was added solution of compound 36 (3.0 g 12.34 mmol) in THF (40 mL) at 0° C. and stirred at rt for 16 hours. The reaction mixture was quenched with brine solution and filtered through a Celite® bed. The organic layer was dried over anhydrous Na2SO4 and evaporated. The crude was purified by Combiflash® chromatography eluting with 2-3% of methanol-DCM to provide liquid compound 37.

Workup

  1. customThe reaction mixture was quenched with brine solution
  2. filtrationfiltered through a Celite® bed
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. customevaporated
  5. customThe crude was purified by Combiflash® chromatography
  6. washeluting with 2-3% of methanol-DCM

Sources & evidence

ORD record
ord-64435035e7a14d5e8ac8acbe37a2eeae
Source dataset
uspto-grants-2015_06
Patent number
US09044482B2

Reaction notes

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