tert-butyl N-(4-aminobutyl)carbamate → {4-[(3-Phenyl-pyridin-2-ylmethyl)-amino]-butyl}-carbamic acid tert-butyl ester

HRID 251090Notes

Reaction equation

HRID 251090 reaction equation
[C:1]1([C:7]2[C:8]([CH:13]=O)=[N:9][CH:10]=[CH:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15]([O:19][C:20](=[O:27])[NH:21][CH2:22][CH2:23][CH2:24][CH2:25][NH2:26])([CH3:18])([CH3:17])[CH3:16].[BH4-].[Na+]>CO>[C:15]([O:19][C:20](=[O:27])[NH:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][CH2:13][C:8]1[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:12][CH:11]=[CH:10][N:9]=1)([CH3:18])([CH3:16])[CH3:17]

Participants

5

Reactant 3

HCID 4351tert-butyl N-(4-aminobutyl)carbamateHCID 4311764Sodium borohydrideHCID 107738083-Phenyl-2-pyridinecarboxaldehyde

Product 1

HCID 67271656{4-[(3-Phenyl-pyridin-2-ylmethyl)-amino]-butyl}-carbamic acid tert-butyl esterYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An anhydrous MeOH solution (2.0 mL) of 3-phenyl-pyridine-2-carbaldehyde (38 mg, 0.21 mmol) (Iqbal, N. et al. J. Med. Chem. 1998, 41, 1827-1837) and (4-Amino-butyl)-carbamic acid tert-butyl ester (40 mg, 0.21 mmol) was stirred overnight at room temperature, after which NaBH4 (16 mg, 0.41 mmol) was added and the reaction mixture stirred for an additional hour. The solvent was removed in vacuo and the residue dissolved in CH2Cl2 (15 mL) and treated with saturated aqueous NaHCO3 (25 mL). The aqueous layer was separated and extracted with CH2Cl2 (2×15 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo to afford {4-[(3-Phenyl-pyridin-2-ylmethyl)-amino]-butyl}-carbamic acid tert-butyl ester (59 mg, 0.17 mmol) as a yellow oil. The yellow oil was used without further purification.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in CH2Cl2 (15 mL)
  3. additiontreated with saturated aqueous NaHCO3 (25 mL)
  4. customThe aqueous layer was separated
  5. extractionextracted with CH2Cl2 (2×15 mL)
  6. dry with materialThe combined organic extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c187532e204a4205b1dcce9843ee8dbd
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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