Benzyl Bromide → 2-(Tert-butoxycarbonylamino)-5-phenoxyindan

HRID 48421Notes

Reaction equation

HRID 48421 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:18])[CH:15]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].C(Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CC(C)=O>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:18][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:15]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 22719625HCID 22719625, compound

Product 1

HCID 227195862-(Tert-butoxycarbonylamino)-5-phenoxyindanYield 90%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-(tert-butoxycarbonylamino)-5-hydroxyindan (100 mg, 0.40 mmol) synthesized in the above Reference Production Example 1 was dissolved in acetone (2 ml), to which potassium carbonate (58 mg, 0.45 mmol) and benzylbromide (48 μl, 0.40 mmol) were added, and the mixture was heated to reflux for 3 hours. The reaction mixture was extracted with ether and dried, and then the solvent was distilled off under reduced pressure to obtain 2-(tert-butoxycarbonylamino)-5-phenoxyindan (120 mg, 0.36 mmol) having the following physical properties:

Workup

  1. additionwere added
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 3 hours
  4. extractionThe reaction mixture was extracted with ether
  5. customdried
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-053fc30e6b724abc8a11c9c550411c9f
Source dataset
uspto-grants-2004_03
Patent number
US06703421B1

Reaction notes

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