Diethyl Ether → (R)-1-(2-bromoethyl)nipecotic acid ethyl ester hydrobromide

HRID 249431Notes

Reaction equation

HRID 249431 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C@@H:5]1[CH2:10][CH2:9][CH2:8][N:7]([CH2:11][CH2:12]O)[CH2:6]1)[CH3:2].S(Br)([Br:17])=O.C(OCC)C>C1(C)C=CC=CC=1>[BrH:17].[CH2:1]([O:3][C:4](=[O:14])[C@@H:5]1[CH2:10][CH2:9][CH2:8][N:7]([CH2:11][CH2:12][Br:17])[CH2:6]1)[CH3:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 68176Thionyl bromideHCID 54103225(R)-1-(2-hydroxyethyl)nipecotic acid ethyl ester

Product 1

HCID 70009171(R)-1-(2-bromoethyl)nipecotic acid ethyl ester hydrobromideYield 131.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A sample of the above alcohol (140 g, 0.70 mole) was dissolved in toluene (400 ml) and thionyl bromide (80 ml, 0.77 mole) was introduced with vigorous stirring. After 1.5 h the exotherm reaction had subsided and diethyl ether (400 ml) was added. The resultant precipitate was collected by filtration and washed with diethyl ether. The solid was triturated with ethyl acetate, again collected on a filter and dried to provide (R)-1-(2-bromoethyl)nipecotic acid ethyl ester hydrobromide (175 g, 73%) as a white solid, m.p. 210°-215° C.

Workup

  1. customAfter 1.5 h the exotherm reaction
  2. filtrationThe resultant precipitate was collected by filtration
  3. washwashed with diethyl ether
  4. customThe solid was triturated with ethyl acetate
  5. customagain collected on
  6. filtrationa filter
  7. customdried

Sources & evidence

ORD record
ord-f7415f92e936441dbfb95c118c596411
Source dataset
uspto-grants-1993_05
Patent number
US05214057

Reaction notes

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