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N-cyclopropylmethylphthalimide → 3-Hydroxy-2-cyclopropylmethyl-2,3-dihydroisoindol-1-one

HRID 733220
Notes
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Reaction equation

HRID 733220 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9](=[O:10])[C:8]3=[CH:11][CH:12]=[CH:13][CH:14]=[C:7]3[C:6]2=[O:15])[CH2:3][CH2:2]1>CO.[BH4-].[K+].ClCCl>[OH:10][CH:9]1[C:8]2[C:7](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6](=[O:15])[N:5]1[CH2:4][CH:1]1[CH2:2][CH2:3]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 1

HCID 4121050N-cyclopropylmethylphthalimide

Product 1

HCID 179664273-Hydroxy-2-cyclopropylmethyl-2,3-dihydroisoindol-1-oneYield 94.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 4192641Potassium borohydrideSolvent

Conditions

Temperature
20 °C

Procedure

3-Hydroxy-2-cyclopropylmethyl-2,3-dihydroisoindol-1-one is prepared as described in Example 1, starting with 4.3 g of N-cyclopropylmethylphthalimide in 40 cm3 of methanol and 1.2 g of potassium borohydride. The reaction mixture is stirred at a temperature in the region of 20° C. for 20 hours and is then cooled to a temperature in the region of 0° C. and distilled water is added dropwise. The precipitate obtained is filtered off and the solid obtained is then taken up in dichloromethane and concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. 4.1 g of 3-hydroxy-2-cyclopropylmethyl-2,3-dihydroisoindol-1-one are thus obtained in the form of a white powder (Rf=0.38, thin layer chromatography on silica gel, eluent: cyclohexane/ethyl acetate (50/50 by volume)).

Workup

  1. custom3-Hydroxy-2-cyclopropylmethyl-2,3-dihydroisoindol-1-one is prepared
  2. temperatureis then cooled to a temperature in the region of 0° C.
  3. distillationdistilled water
  4. additionis added dropwise
  5. customThe precipitate obtained
  6. filtrationis filtered off
  7. customthe solid obtained
  8. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-f84d6a7e6f444fe1a447af059b864f19
Source dataset
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07589117B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes