Methanol → 1-[4-(Pyrrolidin-1-ylmethyl)phenyl]cyclopropanecarbonitrile

HRID 2275617Notes

Reaction equation

HRID 2275617 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:12]#[N:13])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)=O.[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CO>>[N:14]1([CH2:1][C:3]2[CH:8]=[CH:7][C:6]([C:9]3([C:12]#[N:13])[CH2:11][CH2:10]3)=[CH:5][CH:4]=2)[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 4

HCID 887MethanolHCID 31268PyrrolidineHCID 5049666Sodium triacetoxyborohydrideHCID 866022841-(4-Formylphenyl)cyclopropane-1-carbonitrile

Product 1

HCID 666623631-[4-(Pyrrolidin-1-ylmethyl)phenyl]cyclopropanecarbonitrile

Procedure

A mixture of 1-(4-formylphenyl)cyclopropanecarbonitrile (0.30 g, 0.0018 mol), pyrrolidine (0.18 mL, 0.0021 mol) and sodium triacetoxyborohydride (0.74 g, 0.0035 mol) in methanol (5.0 mL, 0.12 mol) was stirred at rt for 1 h. The reaction was adjusted to be basic (pH=12) and extracted with ethyl acetate. The combined extract was washed with brine, dried, and concentrated to provide the desired product. LC-MS: 227.1 (M+H)+

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe combined extract
  3. washwas washed with brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c8915ad611a54eca960def6651c1cf4e
Source dataset
uspto-grants-2015_09
Patent number
US09126927B2

Reaction notes

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