Triphenylphosphine → HCID 86686319, compound

HRID 1043879Notes

Reaction equation

HRID 1043879 reaction equation
CCOC(/N=N/C(OCC)=O)=O.O[C@@H:14]1[CH2:18][CH2:17][O:16][CH2:15]1.[O:19]=[C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22](=[O:29])[N:21]1[NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[O:29]=[C:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:20](=[O:19])[N:21]1[N:30]([C@H:14]1[CH2:18][CH2:17][O:16][CH2:15]1)[C:31](=[O:37])[O:32][C:33]([CH3:35])([CH3:34])[CH3:36]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 641512(-)-3-HydroxytetrahydrofuranHCID 801162N-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)(tert-butoxy)formamideHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 86686319HCID 86686319, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

DEAD (11.5 mL) was added dropwise to a solution of (R)-(−)-3-hydroxytetrahydrofuran (CAS No. 86087-24-3) (4.84 g), t-butyl (1,3-dioxoisoindolin-2-yl)carbamate (12 g) and triphenylphosphine (18.0 g) in THF (160 mL) under ice-cooling over five minutes. The reaction mixture was stirred at 0° C. for three minutes and then at room temperature for seven hours and 40 minutes. The reaction mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 20%) to give the title compound (12.4 g).

Workup

  1. waitat room temperature for seven hours
  2. custom40 minutes
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 20%)

Sources & evidence

ORD record
ord-eaa5f4a0eed14bf091e359a78a39bf36
Source dataset
uspto-grants-2013_10
Patent number
US08563565B2

Reaction notes

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