Triethylamine → (R)-Methyl 3-(2-methylpropylsulfonamido)-2,3-dihydro-1H-indene-5-carboxylate

HRID 1193280Notes

Reaction equation

HRID 1193280 reaction equation
C(N(CC)CC)C.[NH2:8][C@H:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]([O:20][CH3:21])=[O:19])[CH:16]=2)[CH2:11][CH2:10]1.[CH3:22][CH:23]([CH3:29])[CH2:24][S:25](Cl)(=[O:27])=[O:26]>ClCCl>[CH3:22][CH:23]([CH3:29])[CH2:24][S:25]([NH:8][C@H:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]([O:20][CH3:21])=[O:19])[CH:16]=2)[CH2:11][CH2:10]1)(=[O:27])=[O:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1822361-Propanesulfonyl chloride, 2-methyl-HCID 55278060(R)-Methyl 3-amino-2,3-dihydro-1H-indene-5-carboxylate

Product 1

HCID 66798976(R)-Methyl 3-(2-methylpropylsulfonamido)-2,3-dihydro-1H-indene-5-carboxylateYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (750 μl, 5.15 mmol, 3 eq) was added at 0° C. to a solution of (R)-methyl 3-amino-2,3-dihydro-1H-indene-5-carboxylate (A-07) (1.72 mmol, 1 eq) in dichloromethane (10 ml), and stirring was carried out for 10 min. A solution of 2-methylpropane-1-sulfonyl chloride (404 mg, 2.58 mmol, 1.5 eq), dissolved in dichloromethane (5 ml), was added dropwise, and stirring was carried out for 16 h at RT. After monitoring by thin-layer chromatography, the reaction solution was concentrated under reduced pressure and the residue was purified by column chromatography (silica gel, 30% ethyl acetate in hexane). The desired product was obtained in the form of a white solid. Yield: 93% (500 mg, 1.6 mmol).

Workup

  1. additionwas added dropwise
  2. stirringstirring
  3. waitwas carried out for 16 h at RT
  4. concentrationthe reaction solution was concentrated under reduced pressure
  5. customthe residue was purified by column chromatography (silica gel, 30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-bceaf16701f443999c73c956e54e68f6
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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