Triethylamine → N-[(1R,2R)-2-(tert-butyl-dimethyl-silanyloxy)-indan-1-yl]-methanesulphonamide

HRID 1258169Notes

Reaction equation

HRID 1258169 reaction equation
[C:1]([Si:5]([CH3:18])([CH3:17])[O:6][C@@H:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C@H:8]1[NH2:16])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>C(Cl)Cl>[C:1]([Si:5]([CH3:18])([CH3:17])[O:6][C@@H:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C@H:8]1[NH:16][S:27]([CH3:26])(=[O:29])=[O:28])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58450870(1R,2R)-2-(tert-butyl-dimethyl-silanyloxy)-indan-1-ylamine

Product 1

HCID 58450866N-[(1R,2R)-2-(tert-butyl-dimethyl-silanyloxy)-indan-1-yl]-methanesulphonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(1R,2R)-2-(tert-butyl-dimethyl-silanyloxy)-indan-1-ylamine (1.60 g) is dissolved in 16 mL DCM and combined with triethylamine (2.54 mL). Then methanesulphonyl chloride (0.61 mL in 5 mL DCM) is added dropwise. The reaction mixture is stirred for 2 h and after elimination of the solvent it is purified by normal phase chromatography (cHex/EA). The product-containing fractions are combined and freed from the solvent using the rotary evaporator.

Workup

  1. customafter elimination of the solvent it is purified by normal phase chromatography (cHex/EA)
  2. customthe rotary evaporator

Sources & evidence

ORD record
ord-7c5e9e87087d4343910d21a0354a00c6
Source dataset
uspto-grants-2013_06
Patent number
US08466155B2

Reaction notes

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