Hydrochloric Acid → 3-[(1-Naphthyloxy)methyl]pyrrolidine

HRID 2116606Notes

Reaction equation

HRID 2116606 reaction equation
[C:1]1([O:11][CH2:12][CH:13]2[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Cl>O1CCOCC1>[C:1]1([O:11][CH2:12][CH:13]2[CH2:17][CH2:16][NH:15][CH2:14]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 674164501,1-Dimethylethyl 3-[(1-naphthalenyloxy)methyl]-1-pyrrolidinecarboxylate

Product 1

HCID 450755773-[(1-Naphthyloxy)methyl]pyrrolidineYield 72.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 0.42 g (1.28 mmol) of 1,1-dimethylethyl 3-[(1-naphthalenyloxy)methyl]-1-pyrrolidinecarboxylate, prepared in Step 12.1., in 10 ml of 1,4-dioxane and 6 ml of a 2N solution of aqueous hydrochloric acid is stirred for 6 hours. It is evaporated to dryness and then coevaporation is carried out twice with toluene. The solid residue is washed with diethyl ether. The solid is taken up in dichloromethane and concentrated ammonia solution is added until a basic pH is obtained. The system is filtered on a Whatman PTFE cartridge and the organic phase is concentrated, to give 0.21 g of oily product, which is used as it is in the following step.

Workup

  1. customIt is evaporated to dryness
  2. washThe solid residue is washed with diethyl ether
  3. additionconcentrated ammonia solution is added until a basic pH
  4. customis obtained
  5. filtrationThe system is filtered on a Whatman PTFE cartridge
  6. concentrationthe organic phase is concentrated

Sources & evidence

ORD record
ord-88de0f0ad2ff482d9a42998343b25da0
Source dataset
uspto-grants-2008_10
Patent number
US07439257B2

Reaction notes

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