Acetic Acid → HCID 121005435, compound

HRID 1466018Notes

Reaction equation

HRID 1466018 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]=O)=[CH:6][C:3]=1[C:4]#[N:5].[C:13]([O:17][C:18](=[O:23])[NH:19][CH2:20][CH2:21][NH2:22])([CH3:16])([CH3:15])[CH3:14].[BH3-]C#N.[Na+].C(O)(=O)C>CO>[C:4]([C:3]1[CH:6]=[C:7]([CH2:10][CH2:11][NH:22][CH2:21][CH2:20][NH:19][C:18](=[O:23])[O:17][C:13]([CH3:15])([CH3:14])[CH3:16])[CH:8]=[CH:9][C:2]=1[F:1])#[N:5]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 187201N-BOC-ethylenediamineHCID 5003444Sodium cyanoborohydrideHCID 77231555HCID 77231555, compound

Product 1

HCID 121005435HCID 121005435, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-fluoro-5-(2-oxoethyl)benzonitrile (1.5 g, 9.2 mmol), tert-butyl(2-aminoethyl)carbamate (1.5 g, 9.2 mmol), NaCNBH3 (1.2 g, 18.4 mmol) and acetic acid (1.6 g, 27.6 mmol) in methanol (20 mL) was stirred at ambient temperature overnight. The solvents were evaporated, and the residue was basified with saturated NaHCO3 to pH=7-8, and extracted with EtOAc. The organic layer was separated, dried over anhydrous sodium sulfate and evaporated. The residue was purified with silica gel column chromatography to give tert-Butyl (2-{[2-(3-cyano-4-fluorophenyl)ethyl]amino}ethyl)carbamate.

Workup

  1. customThe solvents were evaporated
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. customThe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-6226cf6fc5104ca09c73b51f8907e782
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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