Water → Benzyl 3,4-dihydroxypyrrolidine-1-carboxylate

HRID 2176954Notes

Reaction equation

HRID 2176954 reaction equation
[C:1]([N:11]1[CH2:15][CH2:14][CH:13]=[CH:12]1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C[N+]1([O-])CC[O:20]CC1.OS([O-])=O.[Na+].[OH2:29]>C1COCC1.CC(O)(C)C.[Os](=O)(=O)(=O)=O>[OH:29][CH:13]1[CH:14]([OH:20])[CH2:15][N:11]([C:1]([O:3][CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:2])[CH2:12]1

Participants

8

Reactant 4

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 11074472Benzyl 2,3-dihydro-1H-pyrrole-1-carboxylateHCID 23665763Sodium Bisulfite

Product 1

HCID 14771964Benzyl 3,4-dihydroxypyrrolidine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a 500 mL RBF, the Cbz Pyrroline (15 g, 73.8 mmol) was dissolved in a mixture of 100 mL THF, 60 mL t-BuOH and 40 mL water for addition of the NMO (30.6 ml, 148 mmol) solution followed by the osmium tetraoxide (0.925 ml, 0.074 mmol) solution. Heated in a 70 C. oil bath. Solution slowly went from yellow to brown. After 2 h, cooled to RT and added 50 mL 10% aqueous NaHSO3. Concentrated and partitioned between 100 mL brine and 100 mL EtOAc. Separated layers and extracted with 100 mL EtOAc. Dried over MgSO4, filtered and concentrated to 22.3 g of thick yellow oil. Flash column chromatography from 50-100% EtOAc in hexane provided compound 9. NMR (400 MHz, CDCl3) δ 7.35 (m, 5H), 5.22 (s, 2H), 4.42 (m, 4H), 3.63 (m, 2H), 3.42 (m, 3H), 3.20 (m, 1H).

Workup

  1. temperatureHeated in a 70 C
  2. concentrationConcentrated
  3. custompartitioned between 100 mL brine and 100 mL EtOAc
  4. extractionSeparated layers and extracted with 100 mL EtOAc
  5. dry with materialDried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to 22.3 g of thick yellow oil

Sources & evidence

ORD record
ord-0c4fea9954e94acfb80d27a84b4343af
Source dataset
uspto-grants-2015_06
Patent number
US09067882B2

Reaction notes

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