Benzyl chloroformate → benzyl N-(5-bromo-2,3-dihydro-1H-inden-1-yl)carbamate

HRID 43016Notes

Reaction equation

HRID 43016 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([NH2:11])[CH2:6][CH2:5]2.C(=O)([O-])[O-].[K+].[K+].Cl[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20]>C(OCC)(=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([NH:11][C:19](=[O:20])[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:6][CH2:5]2

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 222283885-bromo-2,3-dihydro-1H-inden-1-amine

Product 1

HCID 67088086benzyl N-(5-bromo-2,3-dihydro-1H-inden-1-yl)carbamateYield 67.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-bromo-2,3-dihydro-1H-inden-1-amine (23.57 mmol, 5 g) in ethyl acetate (40 mL) was added potassium carbonate (47.1 mmol, 6.52 g) as a solution in water (40.0 mL). The whole was stirred vigorously before benzyl chloroformate (25.9 mmol, 3.65 mL, 4.42 g) was added and stirring continued overnight. The reaction was quenched with more water and was extracted with DCM (2×). The organic layers were separated and dried using a hydrophobic frit, and were concentrated in vacuo to give desired product as a brown solid (5.5 g, 15.9 mmol, 67.4%). 1H NMR (400 MHz, CDCl3) δ 1.82 (m, 1H) 2.60 (m, 1H) 2.85 (m, 1H) 2.90 (m, 1H), 4.95 (d, 1H) 5.18 (m, 3H) 7.18 (d, 1H) 7.34 (m, 7H).

Workup

  1. additionwas added
  2. customThe reaction was quenched with more water
  3. extractionwas extracted with DCM (2×)
  4. customThe organic layers were separated
  5. customdried
  6. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-6ab4b2140bb245ec85f6060ceb15322b
Source dataset
uspto-grants-2013_09
Patent number
US08536214B2

Reaction notes

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