Phthalimide → HCID 12803194, compound

HRID 1904767Notes

Reaction equation

HRID 1904767 reaction equation
[N:1](C(OCC)=O)=NC(OCC)=O.O[CH2:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][CH:19]=[C:18]2[CH2:24][CH2:25][NH:26][C:27](=[O:36])[O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(=O)NC(=O)C2=CC=CC=C12>O1CCCC1>[NH2:1][CH2:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][CH:19]=[C:18]2[CH2:24][CH2:25][NH:26][C:27](=[O:36])[O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 20197302HCID 20197302, compound

Product 1

HCID 12803194HCID 12803194, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of diethyl azodicarboxylate (1.48 g) in dry tetrahydrofuran (THF) (8 ml) was added over 2 min., keeping the temperature at 25°, to a stirred solution of phenylmethyl [2-[5-(-hydroxymethyl)-1H-indol-3-yl]ethyl]-carbamate (2.6 g), triphenylphosphine (2.35 g) and phthalimide (1.75 g) in THF (20 ml). After 4 h, the solvent was evaporated in vacuo and the residue was dissolved in a solution of hydrazine hydrate (15 ml) in ethanol (100 ml).

Workup

  1. customat 25°
  2. customthe solvent was evaporated in vacuo
  3. dissolutionthe residue was dissolved in a solution of hydrazine hydrate (15 ml) in ethanol (100 ml)

Sources & evidence

ORD record
ord-2d0edc92f6514f68b527b8f17661562f
Source dataset
uspto-grants-1989_06
Patent number
US04839377

Reaction notes

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