HCID 16732282, compound → (2S,3S)-N-tert-Butyloxycarbonyl-3-(tert-butyldimethylsilanyloxy)-2-((1R)-1-aminoethyl)pyrrolidine

HRID 501653Notes

Reaction equation

HRID 501653 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[C@H:9]1[C@H:21]([N:23]=[N+]=[N-])[CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.CCOC(C)=O.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[C@@H:9]1[C@H:21]([NH2:23])[CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 16732282HCID 16732282, compound

Product 1

HCID 68457944(2S,3S)-N-tert-Butyloxycarbonyl-3-(tert-butyldimethylsilanyloxy)-2-((1R)-1-aminoethyl)pyrrolidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A mixture of 80C (410 mg, 1.10 mmol) and 10% Pd/C (100 mg) in MeOH:EtOAc (2:1, 15 mL) was stirred under hydrogen atmosphere for 2 h. The reaction was filtered through a pad of celite. The filtrate was concentrated and purified by flash chromatography (10 g ISCO silica gel cartridge, 0-20% MeOH/DCM) to the title compound 80D (284 mg): MS (ES) m/z 345 [M+H]+.

Workup

  1. filtrationThe reaction was filtered through a pad of celite
  2. concentrationThe filtrate was concentrated
  3. custompurified by flash chromatography (10 g ISCO silica gel cartridge, 0-20% MeOH/DCM) to the title compound 80D (284 mg)

Sources & evidence

ORD record
ord-82017d5bed5c41d7a3d31499c2046763
Source dataset
uspto-grants-2010_08
Patent number
US07772267B2

Reaction notes

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