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Benzyl chloroformate → ((S)-5-bromo-indan-2-yl)-carbamic acid benzyl ester

HRID 42995
Notes
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Reaction equation

HRID 42995 reaction equation
CC1(C)[C@H]2CC[C@]1(CS(O)(=O)=O)C(=O)C2.[Br:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[CH2:22][C@H:21]([NH2:26])[CH2:20]2.C(=O)([O-])[O-].[K+].[K+].Cl[C:34]([O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:35]>CCOC(C)=O.O>[Br:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[CH2:22][C@H:21]([NH:26][C:34](=[O:35])[O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH2:20]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 46899972(S)-5-bromo-2,3-dihydro-1H-inden-2-amine ((1R,4S)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonate

Product 1

HCID 57831316((S)-5-bromo-indan-2-yl)-carbamic acid benzyl esterYield 108%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
2×
HCID 8857Ethyl AcetateSolvent2×

Procedure

(S)-5-bromo-2,3-dihydro-1H-inden-2-amine((1R,4S)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonate (18.47 mmol, 8.21 g) was dissolved in EtOAc (30 mL)/water (30 mL) and potassium carbonate (55.4 mmol, 7.66 g) added. The mixture was cooled in an ice bath and benzyl chloroformate (20.32 mmol, 2.89 mL, 3.47 g) added dropwise. Stirring was continued overnight during which time the reaction came to room temperature. The crude reaction mixture was diluted with water and ethylacetate and the phases mixed and separated. The aqueous layer was further extracted with EtOAc (×2). Combined organics were dried and concentrated to give (S)-benzyl 5-bromo-2,3-dihydro-1H-inden-2-ylcarbamate as a colourless solid (6.89 g, 108%). 1H NMR (400 MHz, CDCl3) δ 2.79 (m, 2H) 3.26 (m, 2H) 4.53 (bm, 1H) 4.93 (bm, 1H) 5.10 (bs, 2H) 7.07 (m, 1H) 7.26-7.37 (m, 7H)

Workup

  1. additionadded
  2. temperatureThe mixture was cooled in an ice bath
  3. customcame to room temperature
  4. customThe crude reaction mixture
  5. additionthe phases mixed
  6. customseparated
  7. extractionThe aqueous layer was further extracted with EtOAc (×2)
  8. customCombined organics were dried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-4020e718786a49f1ac78715d6048857f
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08536214B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes