rac-(1R,2R)-2-(4-nitrophenyl)cyclopropane-1-carboxylic acid → (1R,2R)-2-(4-aminophenyl)cyclopropane-1-carboxylic acid

HRID 1173044Notes

Reaction equation

HRID 1173044 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]2[CH2:12][C@H:11]2[C:13]([OH:15])=[O:14])=[CH:6][CH:5]=1)([O-])=O.O.O.[Sn](Cl)(Cl)(Cl)Cl>CN1CCCC1=O>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C@@H:10]2[CH2:12][C@H:11]2[C:13]([OH:15])=[O:14])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 12854631rac-(1R,2R)-2-(4-nitrophenyl)cyclopropane-1-carboxylic acidHCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 68668314(1R,2R)-2-(4-aminophenyl)cyclopropane-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a suspension of the Wang resin-supported racemic-(trans)-2-(4-nitrophenyl)cyclopropanecarboxylic acid (XIIc) in N-methylpyrrolidin-2-one (NMP, ˜15 ml/mmol) was added tin chloride dihydrate (15 equiv.). The mixture was shaken for 67 h and then filtered. The product resin was washed with NMP (×2), DCM, dioxane, dioxane-water (1:1×2), water (×2), dioxane-water (1:1×2) dioxane (×3), DCM (×3), methanol and ether, then dried in a vacuum oven at 40° C.

Workup

  1. filtrationfiltered
  2. washThe product resin was washed with NMP (×2), DCM, dioxane, dioxane-water (1:1×2), water (×2), dioxane-water (1:1×2) dioxane (×3), DCM (×3), methanol and ether
  3. customdried in a vacuum oven at 40° C.

Sources & evidence

ORD record
ord-142218640d0f48a6841875fd86097a19
Source dataset
uspto-grants-2010_11
Patent number
US07834013B2

Reaction notes

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