Sodium Hydroxide → Boc-Hyp(Bzl)-OH

HRID 525045Notes

Reaction equation

HRID 525045 reaction equation
[CH2:1]([O:8][C@H:9]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@H:11]([C:21]([O:23]C)=[O:22])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO.C1COCC1>[CH2:1]([O:8][C@H:9]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:19])([CH3:20])[CH3:18])=[O:15])[C@H:11]([C:21]([OH:23])=[O:22])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 148639421-tert-Butyl 2-methyl (2S,4R)-4-(benzyloxy)pyrrolidine-1,2-dicarboxylate

Product 1

HCID 11860409Boc-Hyp(Bzl)-OHYield 76%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

(2S,4R)-1-tert-Butyl 2-methyl 4-(benzyloxy)pyrrolidine-1,2-dicarboxylate (2.78 g, 8.29 mmol) was dissolved in a 1:1 mixture of MeOH and THF (30 ml) and 2N NaOH (12.5 ml, 26 mmol) was added. After stirring at room temperature for 2 h, the organic solvents were evaporated under reduced pressure and the aqueous phase was extracted twice with dichloromethane. The aqueous phase was then cooled at 0° C. and then acidified with concentrated chlorhydric acid. This phase was extracted twice with dichloromethane. The organic phase was dried over magnesium sulphate, filtered and the solvent evaporated under reduced pressure. 2.01 g (76% yield) of the final compound were obtained, pure enough to perform the next synthetic step.

Workup

  1. additionwas added
  2. customthe organic solvents were evaporated under reduced pressure
  3. extractionthe aqueous phase was extracted twice with dichloromethane
  4. temperatureThe aqueous phase was then cooled at 0° C.
  5. extractionThis phase was extracted twice with dichloromethane
  6. dry with materialThe organic phase was dried over magnesium sulphate
  7. filtrationfiltered
  8. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-2f7f63b0e972437ab6e50c0898cb9aa2
Source dataset
uspto-grants-2016_05
Patent number
US09340547B2

Reaction notes

Loading…