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

HRID 473103Notes

Reaction equation

HRID 473103 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.O.[C:28](Cl)(=[O:37])[O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CCOC(C)=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:28](=[O:37])[O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:20]2

Participants

5

Reactant 3

HCID 962WaterHCID 10387Benzyl chloroformateHCID 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 99.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To (S)-5-bromo-2,3-dihydro-1H-inden-2-amine((1R,4S)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonate (13.95 mmol, 6.2 g) in EtOAc (93 mL)/Water (93 mL) was added benzyl carbonochloridate (15.35 mmol, 2.62 g) dropwise at 0° C. under an argon atmosphere. The reaction was left to stir for 18 hrs. The aqueous layer was removed before washing the organic with brine. The organics were dried over MgSO4 before filtering and removing the solvent in vacuo to give the title compound as a white solid (4.8 g, 99%). 1H NMR (400 MHz, CDCl3) δ 2.79 (m, 2H), 3.25 (m, 2H), 4.53 (d, 1H), 4.93 (brs, 1H), 5.10 (s, 2H), 7.08 (d, 1H) 7.31 (m, 7H).

Workup

  1. waitThe reaction was left
  2. customThe aqueous layer was removed
  3. washbefore washing the organic with brine
  4. dry with materialThe organics were dried over MgSO4
  5. filtrationbefore filtering
  6. customremoving the solvent in vacuo

Sources & evidence

ORD record
ord-67e3753045dc49e78ed91c10fa5e63b6
Source dataset
uspto-grants-2014_01
Patent number
US08633237B2

Reaction notes

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