L-Prolinol → 4-[(2S)-2-(Hydroxymethyl)pyrrolidin-1-yl]naphthalene-1-carbonitrile

HRID 916314Notes

Reaction equation

HRID 916314 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[CH2:20][CH2:19][CH2:18][C@H:15]1[CH2:16][OH:17]>C1(C)C=CC=CC=1>[OH:17][CH2:16][C@@H:15]1[CH2:18][CH2:19][CH2:20][N:14]1[C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]([C:1]#[N:2])=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 640091L-ProlinolHCID 27367341-Cyano-4-fluoronaphthalene

Product 1

HCID 247436414-[(2S)-2-(Hydroxymethyl)pyrrolidin-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 L-prolinol (197 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 flash chromatography on silica gel (eluent: 0-3% methanol in dichloromethane). Yield: 23 mg (18%).

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 flash chromatography on silica gel (eluent: 0-3% methanol in dichloromethane)

Sources & evidence

ORD record
ord-c8fe259f9c5c45eca2a52ce2648f51de
Source dataset
uspto-grants-2007_09
Patent number
US07268232B2

Reaction notes

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