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Benzyl Alcohol → 2-(Benzyloxycarbonylaminomethyl)indan

HRID 1289437
Notes
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Reaction equation

HRID 1289437 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 1140
Toluene
Solvent

Procedure

Dissolved in 150 ml of toluene were 17.6 g (0.10 mol) of 2-(indan-2-yl)acetic acid, and 15.3 ml (0.11 mol) of triethyl-amine and 33.0 g (0.12 mol) of diphenylphosphoryl azide were added to the solution. After the mixture was stirred at room temperature for 30 minutes, 16.6 g (0.15 mol) of benzyl alcohol were added, and the resultant mixture was refluxed for 18 hours. After cooling the mixture, the solvent was distilled off under reduced pressure, and the residue was dissolved in 500 ml of ethyl acetate, washed with 1N sodium hydroxide and then concentrated. The resultant residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:3), and the resultant crystal was recrystallized from a mixed solvent of ethyl acetate and hexane to obtain 24.3 g of 2-(benzyloxycarbonylamino-methyl)indane as a colorless needle crystal. Yield: 86%.

Workup

  1. additionwere added to the solution
  2. temperatureAfter cooling the mixture
  3. distillationthe solvent was distilled off under reduced pressure
  4. dissolutionthe residue was dissolved in 500 ml of ethyl acetate
  5. washwashed with 1N sodium hydroxide
  6. concentrationconcentrated
  7. customThe resultant residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:3)
  8. customthe resultant crystal was recrystallized from a mixed solvent of ethyl acetate and hexane

Sources & evidence

ORD record
ord-1de21c5e1be641ceb804a768ed55cbd6
Source dataset
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05750524

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes