9-Fluorenylmethyl chloroformate → (9H-Fluoren-9-yl)methyl (3-bromopropyl)carbamate

HRID 1005586Notes

Reaction equation

HRID 1005586 reaction equation
Br.[Br:2][CH2:3][CH2:4][CH2:5][NH2:6].C(N(C(C)C)CC)(C)C.[CH:16]1[C:28]2[CH:27]([CH2:29][O:30][C:31](Cl)=[O:32])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]=2[CH:19]=[CH:18][CH:17]=1>ClCCl>[CH:16]1[C:28]2[CH:27]([CH2:29][O:30][C:31]([NH:6][CH2:5][CH2:4][CH2:3][Br:2])=[O:32])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]=2[CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 343679-Fluorenylmethyl chloroformateHCID 787013-Bromopropylamine hydrobromideHCID 81531Diisopropylethylamine

Product 1

HCID 16218514(9H-Fluoren-9-yl)methyl (3-bromopropyl)carbamateYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-bromopropylamine hydrobromide (5.0 g) and diisopropylethylamine (5.90 g) in dichloromethane (80 ml) was added portionwise 9-fluorenylmethoxycarbonyl chloride (5.91 g) and the mixture was stirred at ambient temperature for 3 hours and stand overnight. The resulting mixture was diluted with dichloromethane (50 ml) and the organic layer was washed successively with 1N hydrochloric acid and brine. Drying, filtering and removal of solvents afforded a crude product. The crude product was triturated with diethyl ether-hexane (1:5) to give 3-(9-fluorenylmethoxycarbonylamino)propyl bromide (7.82 g).

Workup

  1. waitstand overnight
  2. washthe organic layer was washed successively with 1N hydrochloric acid and brine
  3. customDrying
  4. filtrationfiltering
  5. customremoval of solvents
  6. customafforded a crude product
  7. customThe crude product was triturated with diethyl ether-hexane (1:5)

Sources & evidence

ORD record
ord-ce10aff9c11546a8884f0c2290356816
Source dataset
uspto-grants-2000_04
Patent number
US06054457

Reaction notes

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