(2-Thienylmethyl)amine → HCID 60680143, compound

HRID 1162563Notes

Reaction equation

HRID 1162563 reaction equation
[C:1]([O:5][C:6](=[O:9])[CH2:7]Br)([CH3:4])([CH3:3])[CH3:2].[NH2:10][CH2:11][C:12]1[S:13][CH:14]=[CH:15][CH:16]=1.CCN(C(C)C)C(C)C>C1COCC1.CCOCC>[C:1]([O:5][C:6](=[O:9])[CH2:7][NH:10][CH2:11][C:12]1[S:13][CH:14]=[CH:15][CH:16]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 34005(2-Thienylmethyl)amineHCID 79177tert-Butyl bromoacetateHCID 81531Diisopropylethylamine

Product 1

HCID 60680143HCID 60680143, compoundYield 52.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

t-Butylbromoacetate (1.45 mL, 10 mmol) was added to 2-aminomethyl thiophene (1.13 g. 10.0 mmol) and DIEA (2.0 ml) in THF (20 mL). The mixture was warmed to room temperature (4 h), diluted with ether (100 mL) and washed with water (20 mL), brine (20 mL), dried (MgSO4), filtered and evaporated in vacuum. The product was purified by column chromatography eluting with 10-25% EtOAc in hexane to give [(thiophen-2-ylmethyl)-amino]-acetic acid tert-butyl ester (1.2 g). LCMS m/z: 229 (M+1)+.

Workup

  1. washwashed with water (20 mL), brine (20 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated in vacuum
  5. customThe product was purified by column chromatography
  6. washeluting with 10-25% EtOAc in hexane

Sources & evidence

ORD record
ord-0d77e5c9e4f04ab99d8ed5bf1b331c71
Source dataset
uspto-grants-2010_10
Patent number
US07820704B2

Reaction notes

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