Sodium Hydroxide → 3-Hydroxy-hexahydro-pyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester

HRID 1965186Notes

Reaction equation

HRID 1965186 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13]C(=O)C2C=CC([N+]([O-])=O)=CC=2)[CH:10]2[N:25]([C:28]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[O:29])[CH2:26][CH2:27][CH:9]12)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1.CO>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([OH:13])[CH:10]2[N:25]([C:28]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[O:29])[CH2:26][CH2:27][CH:9]12)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 676070203-(4-Nitro-benzoyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester

Product 1

HCID 676073943-Hydroxy-hexahydro-pyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl esterYield 88%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

The crude ester (42, 11.7 g crude, ˜11.0 mmol) was dissolved in 1:1 THF/MeOH (75 mL) and cooled to 0° C. and 1M NaOH (45 mL) was added in one portion. After 45 min, the reaction mixture was quenched with glacial HOAc (10 mL) and concentrated in vacuo. The residue was dissolved in EtOAc and the organic solution was washed successively with aqueous NaHCO3 (5×) and brine, dried over anhydrous Na2SO4, filtered, and concentrated. The crude product was absorbed onto silica gel and purified by flash silica gel chromatography (2:1 to 1:2 hexanes/EtOAc) to provide 43 as a white foam (3.5 g, 88%, 2 steps): 1H NMR (300 MHz, CDCl3): δ7.39 (m, 5H), 5.15 (m, 2H), 4.40 (m, 2H), 4.13 (m, 1H), 3.54 (m, 3H), 3.35 (m, 1H), 2.83 (m, 1H), 2.11 (m, 2H), 1.49 (s, 9H) ppm. Mass spectrum, m/z [306.6] (M−t-Bu)+.

Workup

  1. customthe reaction mixture was quenched with glacial HOAc (10 mL)
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in EtOAc
  4. washthe organic solution was washed successively with aqueous NaHCO3 (5×) and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was absorbed onto silica gel
  9. custompurified by flash silica gel chromatography (2:1 to 1:2 hexanes/EtOAc)

Sources & evidence

ORD record
ord-56df0870535d48d1b2a86c166dacc525
Source dataset
uspto-grants-2013_04
Patent number
US08415486B2

Reaction notes

Loading…