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Phthalimide → 2-[4-(1-Tertbutoxycarbonylpiperidin-4-yl)-butyl]-isoindol-1,3-dione

HRID 1294463
Notes
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Reaction equation

HRID 1294463 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][CH2:17]O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:38]1(=[O:48])[NH:42][C:41](=[O:43])[C:40]2=[CH:44][CH:45]=[CH:46][CH:47]=[C:39]12.C(OC(N=NC(OCC)=O)=O)C>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][CH2:16][CH2:17][N:42]2[C:38](=[O:48])[C:39]3[C:40](=[CH:44][CH:45]=[CH:46][CH:47]=3)[C:41]2=[O:43])[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2784670tert-Butyl 4-(4-hydroxybutyl)piperidine-1-carboxylate

Product 1

HCID 184257562-[4-(1-Tertbutoxycarbonylpiperidin-4-yl)-butyl]-isoindol-1,3-dione

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
15 °C

Procedure

136 g (<528 mmol) 4-[1-tert-butoxycarbonylpiperidin-4-yl)-butan-1-ol (crude product), 135.3 g (516 mmol) Triphenylphosphine and 75.9 g (516 mmol) phthalimide are suspended in 1800 ml THF and 89.9 g (516 mmol) azodicarboxylic acid diethyl ester are added dropwise within three hours under protective atmosphere and light cooling (to ca. 15° C.). The mixture is left to stand at RT overnight without further cooling. Subsequently, the solvent is removed under vacuum and the oily residue is dissolved in 500 ml acetic acid ethyl ester and held at 0° C. overnight. The sedimented precipitate is filtered and discarded. The solution is concentrated under vacuum and the oily residue is chromatographically purified over silica gel with CHCl3 and crystallized from 200 ml isopropanol after drawing off the solvent. Colorless crystals remain with a MP of 100–102° C.; yield: 108.5 g (57%).

Workup

  1. waitThe mixture is left
  2. customSubsequently, the solvent is removed under vacuum
  3. dissolutionthe oily residue is dissolved in 500 ml acetic acid ethyl ester
  4. waitheld at 0° C. overnight
  5. filtrationThe sedimented precipitate is filtered
  6. concentrationThe solution is concentrated under vacuum
  7. customthe oily residue is chromatographically purified over silica gel with CHCl3
  8. customcrystallized from 200 ml isopropanol

Sources & evidence

ORD record
ord-66d01216535f4392b9239d22be161e03
Source dataset
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07241745B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes