HCID 15537958, compound → HCID 54038063, compound

HRID 620790Notes

Reaction equation

HRID 620790 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:13][N:12](C(OCC2C=CC([N+]([O-])=O)=CC=2)=O)[C@H:11]([CH2:27][OH:28])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>[Pd].CO>[Si:1]([O:8][C@H:9]1[CH2:13][NH:12][C@H:11]([CH2:27][OH:28])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 15537958HCID 15537958, compound

Product 1

HCID 54038063HCID 54038063, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (2S,4R)-4-t-butyldimethylsilyloxy-2-hydroxymethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (10.0 g), methanol (100 ml) and 10% palladium on carbon (1.0 g), was stirred in a nitrogen stream at ambient temperature for 3 hours. The catalyst was filtered off and the filtrate was concentrated under reduced pressure to give (2S,4R)-4-t-butyldimethylsilyloxy-2-hydroxymethylpyrrolidine. To a solution of the compound obtained above in tetrahydrofuran (100 ml) was added di-t-butyl dicarbonate (5.60 g) and the mixture was refluxed for 30 minutes. The reaction mixture was concentrated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (160 g) and eluted with chloroform to give (2S,4R)-1-t-butoxycarbonyl-4-t- butyldimethylsilyloxy-2-hydroxymethylpyrrolidine (7.97 g).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e608fcfc47034472b1ea921bf9daade5
Source dataset
uspto-grants-1989_04
Patent number
US04822787

Reaction notes

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