Propargyl bromide → HCID 45087248, compound

HRID 380883Notes

Reaction equation

HRID 380883 reaction equation
[OH:1][C@@H:2]1[CH2:6][CH2:5][NH:4][CH2:3]1.CCN(CC)CC.[CH2:14](Br)[C:15]#[CH:16]>C(Cl)Cl>[OH:1][C@@H:2]1[CH2:6][CH2:5][N:4]([CH2:16][C:15]#[CH:14])[CH2:3]1

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 8471TriethylamineHCID 2759337(R)-3-Pyrrolidinol

Product 1

HCID 45087248HCID 45087248, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-3-hydroxy-pyrrolidine (2.00 g, 22.95 mmol) (Aldrich) and Et3N (9.00 g, 88.93 mmol) in 45 mL of CH2Cl2 at 0° C. it was added propargyl bromide (3.00 g, 25.21 mmol) in a dropwise manner. Upon completion of the addition, the reaction mixture was filtered and the filtrate was washed with brine, dried over Na2SO4 and concentrated. (R)-3-Hydroxy-1-prop-2-ynyl-pyrrolidine was obtained after Krugerhor distitation (Yield 700 mg, 24%).

Workup

  1. additionUpon completion of the addition
  2. filtrationthe reaction mixture was filtered
  3. washthe filtrate was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7f7d9721b9a54538a32d4d911f0ea3b5
Source dataset
uspto-grants-2001_10
Patent number
US06303793B1

Reaction notes

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