Phthalimide → HCID 22038194, compound

HRID 1790432Notes

Reaction equation

HRID 1790432 reaction equation
[N:1](C(OCC)=O)=NC(OCC)=O.[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([N:26]2[C:34]3[C:29](=[CH:30][CH:31]=[C:32]([CH2:35]O)[CH:33]=3)[CH2:28][CH2:27]2)[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(=O)NC(=O)C2=CC=CC=C12>O1CCCC1>[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([N:26]2[C:34]3[C:29](=[CH:30][CH:31]=[C:32]([CH2:35][NH2:1])[CH:33]=3)[CH2:28][CH2:27]2)[CH2:22][CH2:21]1)=[O:19])([CH3:14])([CH3:15])[CH3:16]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 22038294HCID 22038294, compound

Product 1

HCID 22038194HCID 22038194, compoundYield 105.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under ice cooling, a solution of diethyl azodicarboxylate (4.6 g) in tetrahydrofuran (20 ml) was added dropwise into a solution of 1-[1-(t-butoxycarbonyl)piperidin-4-yl]-6-hydroxymethylindoline (7.9 g), triphenylphosphine (6.9 g) and phthalimide (3.9 g) in tetrahydrofuran (250 ml) and the resultant mixture was stirred at room temperature for 3 hr. After concentrating under reduced pressure, the resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system). Then hydrazine hydrate (3.6 g) and ethanol (150 ml) were added thereto followed by healing under reflux for 2 hr. After ice cooling, the resulting crystalline precipitates were filtered off and the filtrate was concentrated under reduced pressure to give the title compound (8.3 g).

Workup

  1. concentrationAfter concentrating under reduced pressure
  2. customthe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system)
  3. additionThen hydrazine hydrate (3.6 g) and ethanol (150 ml) were added
  4. temperatureunder reflux for 2 hr
  5. customAfter ice cooling, the resulting crystalline precipitates
  6. filtrationwere filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f74630e205be4e358ba34415d369db12
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

Loading…