HCID 15038587, compound → HCID 57219732, compound

HRID 2099356Notes

Reaction equation

HRID 2099356 reaction equation
[OH:1][C@H:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:4]([C:14](N(OC)C)=[O:15])[CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C.O1CCCC1>[CH:14]([C@@H:4]1[CH2:3][C@@H:2]([OH:1])[CH2:6][N:5]1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[O:15]

Participants

5

Reactant 2

HCID 15038587HCID 15038587, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 57219732HCID 57219732, compoundYield 63.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

0.9 g of tert-butyl (2S,4R)-4-hydroxy-2-{[methoxy(methyl)amino]carbonyl}pyrrolidine-1-carboxylate is dissolved in 31 ml of diethyl ether under N2. The reaction medium is placed at 0° C. and 3.41 ml of 1N lithium aluminium hydride in tetrahydrofuran is carefully added. The mixture is stirred at 0° C. for 2 h. After hydrolysis with an aqueous potassium sulphate solution, extraction is carried out with diethyl ether until the aqueous phase is completely depleted. Drying over MgSO4 and concentration to dryness are carried out. The crude obtained is chromatographed on silica gel, elution being carried out with a 9/1 mixture of dichloromethane and methanol. 0.45 g of tert-butyl (2S,4R)-2-formyl-4-hydroxypyrrolidine-1-carboxylate is obtained.

Workup

  1. customis placed at 0° C.
  2. customAfter hydrolysis
  3. extractionwith an aqueous potassium sulphate solution, extraction
  4. dry with materialDrying over MgSO4 and concentration to dryness
  5. customThe crude obtained
  6. customis chromatographed on silica gel, elution
  7. additionbeing carried out with a 9/1 mixture of dichloromethane and methanol

Sources & evidence

ORD record
ord-cdeab19a13bd45ffb7a4518777df9f77
Source dataset
uspto-grants-2009_08
Patent number
US07569582B2

Reaction notes

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