p-Toluenesulfonic acid monohydrate → (2R,3R)-N-Boc-3-amino-pent-4-yne-2-ol

HRID 366754Notes

Reaction equation

HRID 366754 reaction equation
[C:1]([N:8]1[C@H:12]([C:13]#[CH:14])[C@@H:11]([CH3:15])[O:10]C1(C)C)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[C:1]([NH:8][C@H:12]([C:13]#[CH:14])[C@H:11]([OH:10])[CH3:15])([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 12970128275387-85-4

Product 1

HCID 21971742(2R,3R)-N-Boc-3-amino-pent-4-yne-2-olYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (4R,5R)-N-boc-4-ethynyl-2,2,5-trimethyl-oxazolidine (1.60 g 6.69 mmol) (Example 102B) and p-toluenesulfonic acid monohydrate (130 mg 0.67 mmol) in MeOH (70 mL) was heated at refluxed. After stirring overnight the solvent was concentrated and the residue was chromatographed directly on a silica gel column with a 0-40% EtOAc in hexanes gradient. This afforded the product (Yield 1.10 g, 83%) as well as recovered starting material (220 mg, 14%).

Workup

  1. temperatureat refluxed
  2. concentrationwas concentrated
  3. customthe residue was chromatographed directly on a silica gel column with a 0-40% EtOAc in hexanes gradient

Sources & evidence

ORD record
ord-13b645c71ffb4ad4bbec984027e57621
Source dataset
uspto-grants-2000_10
Patent number
US06130239

Reaction notes

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