Triethylamine → HCID 86590533, compound

HRID 722272Notes

Reaction equation

HRID 722272 reaction equation
[NH2:1][C@@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@@H:3]1[OH:11].C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>C1COCC1>[CH3:19][S:20]([NH:1][C@@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@@H:3]1[O:11][S:20]([CH3:19])(=[O:22])=[O:21])(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2725045(1R,2S)-(+)-cis-1-Amino-2-indanol

Product 1

HCID 86590533HCID 86590533, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(1R,2S)-1-Amino-2-hydroxyindan (3.0 g, 20mmol) was dissolved in dry THF (40 ml) and triethylamine (8.4 ml, 60.0 mmol) at 10° C. Methane sulphonyl chloride (5.0 g, 44.0 mmol) dissolved in THF (10 ml) was added at such a rate that the internal temperature remained below 15° C. Following the addition the mixture was stirred at room temperature for 20 hours and then evaporated. To the residue was added EtOAc (100 ml) and the mixture washed with saturated aqueous sodium bicarbonate and then water. The organic solution was dried over magnesium sulphate and evaporated to give (1R,2S)-1-methanesulphonamido-2-methylsulphonyloxyindan (5.7 g, 93%) as a pale yellow solid.

Workup

  1. customat 10° C
  2. additionwas added at such a rate that the internal temperature
  3. customremained below 15° C
  4. additionthe addition the mixture
  5. customevaporated
  6. additionTo the residue was added EtOAc (100 ml)
  7. washthe mixture washed with saturated aqueous sodium bicarbonate
  8. dry with materialThe organic solution was dried over magnesium sulphate
  9. customevaporated

Sources & evidence

ORD record
ord-5776be297d7a4a7bb609a747ebe23c39
Source dataset
uspto-grants-2006_11
Patent number
US07138415B2

Reaction notes

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