Acetic Acid → (2S,3R)-tert-Butyl 2-cyclopropyl-3-hydroxy-5-oxopyrrolidine-1-carboxylate

HRID 1011600Notes

Reaction equation

HRID 1011600 reaction equation
[CH:1]1([C@H:4]2[C:8](=[O:9])[CH2:7][C:6](=[O:10])[N:5]2[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:3][CH2:2]1.C(O)(=O)C.[BH4-].[Na+].CCOC(C)=O>C(Cl)Cl>[CH:1]1([C@H:4]2[C@H:8]([OH:9])[CH2:7][C:6](=[O:10])[N:5]2[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 57659759(s)-tert-Butyl 2-cyclopropyl-3,5-dioxopyrrolidine-1-carboxylate

Product 1

HCID 57659767(2S,3R)-tert-Butyl 2-cyclopropyl-3-hydroxy-5-oxopyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-tert-Butyl 2-cyclopropyl-3,5-dioxopyrrolidine-1-carboxylate (15) (4.0 g, 17.62 mmol) was dissolved in CH2Cl2 (90 mL) and acetic acid (10 mL) and cooled to 0° C. NaBH4 (1.33 g, 35.24 mmol) was added in several portions and the reaction stirred for 16 hr at rt. EtOAc (300 mL) was added and the organics were washed with sat. aq. NaHCO3 (300 mL), brine (200 mL), and dried over Na2SO4. Concentration of the solution in vacuo led to isolation of (2S,3R)-tert-butyl 2-cyclopropyl-3-hydroxy-5-oxopyrrolidine-1-carboxylate (16) (1.34 g, 33%) as a white solid.

Workup

  1. washthe organics were washed with sat. aq. NaHCO3 (300 mL), brine (200 mL)
  2. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-24fe7700cade48539f77899f709e48e0
Source dataset
uspto-grants-2011_07
Patent number
US07977368B2

Reaction notes

Loading…