Pyridine → HCID 57090544, compound

HRID 2073254Notes

Reaction equation

HRID 2073254 reaction equation
N1C=CC=CC=1.[C:7]([O:11][C:12]([N:14]1[CH2:18][C@@H:17]([NH:19][S:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=[O:22])=[O:21])[CH2:16][C@H:15]1[CH2:29][OH:30])=[O:13])([CH3:10])([CH3:9])[CH3:8]>ClCCl.CCCCCC.C(OCC)(=O)C.[O-2].[O-2].[O-2].[Cr+6]>[C:7]([O:11][C:12]([N:14]1[CH2:18][C@@H:17]([NH:19][S:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=[O:22])=[O:21])[CH2:16][C@H:15]1[CH:29]=[O:30])=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

7

Reactant 2

HCID 1049PyridineHCID 18638497HCID 18638497, compound

Product 1

HCID 57090544HCID 57090544, compound

Reagents, catalysts & solvents 4

HCID 10219390chromium (VI) trioxideCatalystHCID 6344DichloromethaneSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of pyridine (8.5 ml) in dichloromethane (150 ml) was added chromium trioxide (5.55 g) in an ice bath and the mixture was stirred at room temperature for 1 hour. To the solution were added Celite and a solution of (2S,4S)-1-t-butoxycarbonyl-2-hydroxymethyl-4-phenylsulfonylaminopyrrolidine (3.4 g) in dichloromethane (20 ml) and the mixture was stirred at room temperature for 1 hour. After being diluted with a mixture of n-hexane and ethyl acetate (1:1, 150 ml), the solution was passed through silica gel and the solvent was evaporated in vacuo to give (2S,4S)-1-t-butoxycarbonyl-2-formyl-4-phenylsulfonylaminopyrrolidine as a pale yellow oil.

Workup

  1. additionTo the solution were added Celite
  2. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-5c8b26847e3d48c6abfb8afa2a737ab3
Source dataset
uspto-grants-1990_04
Patent number
US04916152

Reaction notes

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