Dimethyl Sulfide → [Benzyl-(3-hydroxy-1-methyl-indan-5-yl)-amino]-acetic acid ethyl ester

HRID 593268Notes

Reaction equation

HRID 593268 reaction equation
CSC.[CH2:4]([O:6][C:7](=[O:28])[CH2:8][N:9]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[CH:15]([CH3:19])[CH2:14][C:13]2=[O:20])[CH3:5].[O:29]1CCCC1>C(OCC)(=O)C>[CH3:19][CH:15]1[C:16]2[C:12](=[CH:11][C:10]([NH:9][C:21](=[O:29])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:18][CH:17]=2)[C:13](=[O:20])[CH2:14]1.[CH2:4]([O:6][C:7](=[O:28])[CH2:8][N:9]([CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[CH:15]([CH3:19])[CH2:14][CH:13]2[OH:20])[CH3:5]

Participants

6

Reactant 3

HCID 1068Dimethyl Sulfide2×HCID 8028TetrahydrofuranHCID 86703338[Benzyl-(1-methyl-3-oxo-indan-5-yl)-amino]-acetic acid ethyl ester

Product 2

HCID 86703337N-(1-methyl-3-oxo-indan-5-yl)benzamideHCID 86703339[Benzyl-(3-hydroxy-1-methyl-indan-5-yl)-amino]-acetic acid ethyl esterYield 32%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

As presented in the following reaction formula, a mixture of boran (BH3) in methyl sulfide (Me2S; 1.4 mL, 0.014 mol) was added to a solution of [benzyl-(1-methyl-3-oxo-indan-5-yl)-amino]-acetic acid ethyl ester (4 g, 0.011 mol) and tetrahydrofuran (THF; 50 mL), and the reaction mixture was refluxed for 2 hours. The mixture of BH3 in Me2S (1.4 mL, 0.014 mol) was added several times in a divided manner until there was no reactant left. The reaction was terminated with methanol (10 mL) at 0° C. The resulting mixture was heated to room temperature and stirred for 0.5 hours. The mixture was concentrated to give a crude product. The crude product was purified by silica gel (30 g) column chromatography (product of Merck Co., Ltd.) using an eluent of pentane (PE):ethyl acetate (5:1 (by volume)) to give the desired product [benzyl-(3-hydroxy-1-methyl-indan-5-yl)-amino]-acetic acid ethyl ester (1.4 g, yield: 32%).

Workup

  1. temperaturethe reaction mixture was refluxed for 2 hours
  2. additionwas added several times in a divided manner until there
  3. waitleft
  4. customThe reaction was terminated with methanol (10 mL) at 0° C
  5. concentrationThe mixture was concentrated
  6. customto give a crude product
  7. customThe crude product was purified by silica gel (30 g) column chromatography (product of Merck Co., Ltd.)

Sources & evidence

ORD record
ord-50031bec2a3745099e3eb0577959745c
Source dataset
uspto-grants-2016_01
Patent number
US09242928B2

Reaction notes

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