Tert-Butylamine → methyl 3-(tert-butylamino)-2,3-dihydro-1H-indene-5-carboxylate

HRID 1193261Notes

Reaction equation

HRID 1193261 reaction equation
CS(OS(C)(=O)=O)(=O)=O.O[CH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]([O:22][CH3:23])=[O:21])[CH:18]=2)[CH2:13][CH2:12]1.[C:24]([NH2:28])([CH3:27])([CH3:26])[CH3:25]>C(Cl)Cl>[C:24]([NH:28][CH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]([O:22][CH3:23])=[O:21])[CH:18]=2)[CH2:13][CH2:12]1)([CH3:27])([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 81560Methanesulfonic anhydrideHCID 66798754HCID 66798754, compound

Product 1

HCID 66798482methyl 3-(tert-butylamino)-2,3-dihydro-1H-indene-5-carboxylateYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of methanesulfonic acid anhydride (6.79 g, 39.062 mmol, 2.5 eq.) in DCM (20 ml) was added dropwise at −78° C. to a solution of methyl 3-hydroxy-2,3-dihydro-1H-indene-5-carboxylate (3.0 g, 15.625 mmol, 1.0 eq.) and TEA (11.0 ml, 78.125 mmol, 5.0 eq.) in DCM (60 ml) and stirred for 2 hours at the same temperature. tert-Butylamine (16 ml, 156.5 mmol, 10.0 eq.) was slowly added dropwise at −78° C., and the mixture was heated to RT and stirred for 14 hours. The reaction solution was diluted with DCM (100 ml), washed with water (2×50 ml) and sat. NaCl solution (50 ml), dried over sodium sulfate, concentrated under reduced pressure and purified by column chromatography (silica gel, 13% ethyl acetate in hexane). Yield: 32% (1.2 g, 4.858 mmol)

Workup

  1. stirringstirred for 14 hours
  2. washwashed with water (2×50 ml) and sat. NaCl solution (50 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. custompurified by column chromatography (silica gel, 13% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-71a90ad69e524b79be98b7d942445265
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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