Benzyl Alcohol → 2-(Benzyloxycarbonylaminomethyl)indan

HRID 1654939Notes

Reaction equation

HRID 1654939 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[CH2:10]C(O)=O.C([N:16]([CH2:19]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:28])C=CC=CC=1.[CH2:38]([OH:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C1(C)C=CC=CC=1>[CH2:38]([O:45][C:19]([NH:16][CH2:10][CH:2]1[CH2:1][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3]1)=[O:28])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 51749552-(2,3-dihydro-1H-inden-2-yl)acetic Acid

Product 1

HCID 189214832-(Benzyloxycarbonylaminomethyl)indanYield 86.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

17.6 g (0.10 mol) of (indan-2-yl)acetic acid was dissolved in 150 ml of toluene, to which were added 15.3 ml (0.11 mol) of triethylamine and 33.0 g (0.12 mol) of diphenylphosphorylazide, and stirred at room temperature for 30 minutes. The mixture was added with 16.6 g (0.15 mol) of benzyl alcohol and refluxed for 18 hours. After cooling, the solvent was distilled under reduced pressure, and the residue was added with 500 ml of ethyl acetate, washed with 1N sodium hydroxide, and condensed. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:3), and the crystals collected were recrystallized from a solvent mixture of ethyl acetate and hexane to obtain 24.3 g of 2-(benzyloxycarbonylaminomethyl)indan as colorless needles. Yield: 86%

Workup

  1. temperaturerefluxed for 18 hours
  2. temperatureAfter cooling
  3. distillationthe solvent was distilled under reduced pressure
  4. additionthe residue was added with 500 ml of ethyl acetate
  5. washwashed with 1N sodium hydroxide, and condensed
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:3)
  7. customthe crystals collected
  8. customwere recrystallized from a solvent mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-cdd8da38ea0e4a7daae1763de9468670
Source dataset
uspto-grants-1995_04
Patent number
US05409956

Reaction notes

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