Triphenylphosphine → HCID 23289982, compound

HRID 366544Notes

Reaction equation

HRID 366544 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[CH:13]12[CH2:18][CH:17]1[C:16](=[O:19])[NH:15][C:14]2=[O:20].[CH2:21](O)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][OH:28].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[OH:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][N:15]1[C:16](=[O:19])[CH:17]2[CH:13]([CH2:18]2)[C:14]1=[O:20]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 123811,7-HeptanediolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 37200533-Azabicyclo[3.1.0]hexane-2,4-dione

Product 1

HCID 23289982HCID 23289982, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (0.94 g) was added to a mixture of 3-azabicyclo[3.1.0]hexane-2,4-dione (0.5 g), 1,7-heptanediol (2.46 g), triphenylphosphine (1.42 g) and 4 angstrom sieves (1.5 g) in dry tetrahydrofuran (10 ml) under a nitrogen atmosphere. The reaction mixture was stirred at room temperature for 2 days and was then filtered. The solids were washed with ethyl acetate (2×50 ml) and the combined filtrates were evaporated in vacuo. The residue was purified by chromatography on silica using 60-70% ethyl acetate/hexane as eluant, followed by kugelrohr distillation (b.p. 200-220° C. @ 1 mmHg) to give the subtitle compound as a viscous oil.

Workup

  1. filtrationwas then filtered
  2. washThe solids were washed with ethyl acetate (2×50 ml)
  3. customthe combined filtrates were evaporated in vacuo
  4. customThe residue was purified by chromatography on silica using 60-70% ethyl acetate/hexane as eluant
  5. distillationfollowed by kugelrohr distillation (b.p. 200-220° C. @ 1 mmHg)

Sources & evidence

ORD record
ord-bab9c415fe774f6ab7d639fd775ebd7f
Source dataset
uspto-grants-2000_10
Patent number
US06130241

Reaction notes

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