4-Hydroxypyrrolidine → 4-(3-hydroxypyrrolidin-1-yl)naphthalene-1-carbonitrile

HRID 916313Notes

Reaction equation

HRID 916313 reaction equation
[C:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](F)=[CH:5][CH:4]=1)#[N:2].[NH:14]1[CH2:18][CH2:17][CH:16]([OH:19])[CH2:15]1>C1(C)C=CC=CC=1>[OH:19][CH:16]1[CH2:17][CH2:18][N:14]([C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[CH2:15]1

Participants

4

Reactant 2

HCID 982104-HydroxypyrrolidineHCID 27367341-Cyano-4-fluoronaphthalene

Product 1

HCID 116873304-(3-hydroxypyrrolidin-1-yl)naphthalene-1-carbonitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-Cyano-4-fluoronaphthalene (86 mg, 0.5 mmol) was transferred to a Pyrex tube and 3-pyrrolidinol (162 μL, 2.0 mmol) was added followed by toluene (0.5 mL). The tube was capped and the reaction tube was exposed to microwave irradiation (180° C., 5 min). The reaction mixture was concentrated and purified by re-crystallization with EtOH. Yield: 51 mg (43%).

Workup

  1. additionwas added
  2. customThe tube was capped
  3. customthe reaction tube was exposed to microwave irradiation (180° C., 5 min)
  4. concentrationThe reaction mixture was concentrated
  5. custompurified by re-crystallization with EtOH

Sources & evidence

ORD record
ord-a535b74300204e71a7cae9d848daf323
Source dataset
uspto-grants-2007_09
Patent number
US07268232B2

Reaction notes

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