Propargyl bromide → 2-(4-Prop-2-ynyloxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 12924

Reaction equation

HRID 12924 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH2:28](Br)[C:29]#[CH:30]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:30][C:29]#[CH:28])=[CH:17][CH:16]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 59752861(4-Hydroxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 866196562-(4-Prop-2-ynyloxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl esterYield 88.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of the product from step 2 (2.0 g, 6.82 mmol) in anhydrous DMF (50 mL) was added dry K2CO3 (4.6 g, 33 mmol) and allowed to stir for 15 min. Propargyl bromide (1.214 g, 10.20 mmol) in anhydrous DMF (10 mL) was added and the reaction mixture stirred at 50° C. for 6 h, then at rt for 48 h. The reaction mixture was concentrated, taken up in EtOAc, washed with water, dried over anhydrous MgSO4 and the solvent removed in vacuo. The product was purified by silica gel flash chromatography using EtOAc/hexane to obtain the title compound (2.0 g, 88%).

Workup

  1. stirringthe reaction mixture stirred at 50° C. for 6 h
  2. waitat rt for 48 h
  3. concentrationThe reaction mixture was concentrated
  4. washwashed with water
  5. dry with materialdried over anhydrous MgSO4
  6. customthe solvent removed in vacuo
  7. customThe product was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-c118b8ac54d14d2ab9d48661c465d8e7
Source dataset
uspto-grants-2010_06
Patent number
US07728032B2

Linked notes

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