Water → HCID 18669408, compound

HRID 1058849Notes

Reaction equation

HRID 1058849 reaction equation
[NH:1]1[CH2:5][CH2:4][CH:3]([OH:6])[CH2:2]1.CCN(CC)CC.[CH2:14]([O:21][CH2:22][C:23](Cl)=[O:24])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>C(Cl)Cl>[CH2:14]([O:21][CH2:22][C:23]([N:1]1[CH2:5][CH2:4][CH:3]([OH:6])[CH2:2]1)=[O:24])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 982104-HydroxypyrrolidineHCID 177085Benzyloxyacetyl chloride

Product 1

HCID 18669408HCID 18669408, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4.4 mL (52.93 mmol) 3-pyrrolidinol in 250 mL CH2Cl2 at 0° C. was added 8.4 mL (60.26 mmol) NEt3 and 8.2 mL (51.97 mmol) benzyloxyacetyl chloride. The reaction was stirred for 3.5 h and then poured into 400 mL H2O. The reaction was extracted with CH2Cl2, dried over MgSO4, filtered and rotary evaporated to yield 12.0 g (98%) of N-(benzyloxyacetyl)-3-pyrrolidinol as a yellow oil.

Workup

  1. extractionThe reaction was extracted with CH2Cl2
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customrotary evaporated

Sources & evidence

ORD record
ord-2dd9bb289fa348678db00909400130c4
Source dataset
uspto-grants-2003_02
Patent number
US06518285B2

Reaction notes

Loading…