Triethylamine → (1R,2s)-1-(tert-butoxycarbonylamino)-2,3-dihydro-1H-inden-2-yl methanesulfonate

HRID 1244725Notes

Reaction equation

HRID 1244725 reaction equation
[CH3:1][C:2]([CH3:18])([O:4][C:5]([NH:7][C@@H:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][C@@H:9]1[OH:17])=[O:6])[CH3:3].C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>C(Cl)Cl>[CH3:3][C:2]([CH3:18])([O:4][C:5]([NH:7][C@@H:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][C@@H:9]1[O:17][S:27]([CH3:26])(=[O:29])=[O:28])=[O:6])[CH3:1]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 17998891tert-Butyl ((1R,2S)-2-hydroxy-2,3-dihydro-1H-inden-1-yl)carbamate

Product 1

HCID 86338034(1R,2s)-1-(tert-butoxycarbonylamino)-2,3-dihydro-1H-inden-2-yl methanesulfonateYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Cis-1-[(1,1-Dimethylethoxy)carbonylamino]-2-hydroxyindan (Method 5; 14.0 g, 56.2 mmol) was dissolved in DCM (200 ml) and triethylamine (11.8 ml, 84.3 mmol). Methanesulfonyl chloride (7.1 g, 61.9 mmol) dissolved in DCM (20 ml) was added and the mixture stirred at room temperature for 3 hours. The mixture was evaporated and EtOAc (250 ml) added. After washing with water and drying over magnesium sulphate the organic solution was evaporated to yield Cis-1-[(1,1-dimethylethoxy)carbonylamino]-2-methanesulphonyloxyindan (9.7 g, 98%) as a white solid.

Workup

  1. additionwas added
  2. customThe mixture was evaporated
  3. additionEtOAc (250 ml) added
  4. washAfter washing with water
  5. dry with materialdrying over magnesium sulphate the organic solution
  6. customwas evaporated

Sources & evidence

ORD record
ord-8428991341a94547bb9c5f0b4e31a852
Source dataset
uspto-grants-2006_10
Patent number
US07122567B2

Reaction notes

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