(S)-(-)-N-Boc-prolinol → tert-butyl (2S)-2-formylpyrrolidine-1-carboxylate

HRID 2212127Notes

Reaction equation

HRID 2212127 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[C:12]([O:16][C:17]([N:19]1[CH2:23][CH2:22][CH2:21][C@H:20]1[CH2:24][OH:25])=[O:18])([CH3:15])([CH3:14])[CH3:13]>ClCCl>[C:12]([O:16][C:17]([N:19]1[CH2:23][CH2:22][CH2:21][C@H:20]1[CH:24]=[O:25])=[O:18])([CH3:15])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 643448(S)-(-)-N-Boc-prolinolHCID 178418287HCID 178418287, compound

Product 1

HCID 2734674tert-butyl (2S)-2-formylpyrrolidine-1-carboxylateYield 52.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridinium chlorochromate (3.26 g, 15.2 mmol) was added to a solution of (2S)-N-(tert-butoxycarbonyl)-2-(hydroxymethyl)pyrrolidine (2.77 g, 13.8 mmol) in dichloromethane (50 mL) and the mixture was stirred at room temperature for 12 h. The solvent was removed on a rotary evaporator to give a dark brown gum, which was chromatographed, using ethyl acetate:hexane (1:1, v/v) as eluant. Selected fractions containing the product were combined and concentrated on a rotary evaporator to give 1.45 g (52.9% yield) of a colorless oil.

Workup

  1. customThe solvent was removed on a rotary evaporator
  2. customto give a dark brown gum, which
  3. customwas chromatographed
  4. additionSelected fractions containing the product
  5. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-6bb62e48463d4fbab51cc5d8d3591b32
Source dataset
uspto-grants-2006_09
Patent number
US07101896B2

Reaction notes

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