Lithium borohydride → HCID 67420308, compound

HRID 1987349Notes

Reaction equation

HRID 1987349 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([CH2:10][O:11][CH3:12])[CH:7]=[CH:6][C:5]=1[CH2:13][N:14]1[CH:19]([C:20]2[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:18][CH2:17][CH2:16][CH:15]1[C:27]1[C:32]([CH3:33])=[CH:31][CH:30]=[CH:29][N:28]=1.[Li+].[BH4-]>C1COCC1.[OH-].[Na+]>[CH3:26][C:25]1[C:20]([CH:19]2[CH2:18][CH2:17][CH2:16][CH:15]([C:27]3[C:32]([CH3:33])=[CH:31][CH:30]=[CH:29][N:28]=3)[N:14]2[CH2:13][C:5]2[CH:6]=[CH:7][C:8]([CH2:10][O:11][CH3:12])=[CH:9][C:4]=2[CH2:3][OH:2])=[N:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 67422830HCID 67422830, compound

Product 1

HCID 67420308HCID 67420308, compoundYield 84.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 2-(3,3″-dimethyl-3′,4′,5′,6′-tetrahydro-2′H-[2,2′;6′,2″]terpyridin-1′-ylmethyl)-5-methoxymethyl-benzoic acid methyl ester (0.191 g, 0.42 mmol) in THF (8 mL) was added LiBH4 (89 mg, 4.07 mmol) and the mixture was heated to reflux for 3 hours then cooled to room temperature. The mixture was diluted with 1.0 N NaOH (5 mL) and extracted with CH2Cl2 (5×15 mL). The combined organic extracts were dried (Na2SO4) and concentrated. Purification of the crude material by radial chromatography on silica gel (1 mm plate, 20:1:1 CH2Cl2—CH3OH—NH4OH) gave 153 mg (83%) of [2-(3,3″-dimethyl-3′,4′,5′,6′-tetrahydro-2′H-[2,2′;6′,2″]terpyridin-1′-ylmethyl)-5-methoxymethyl-phenyl]-methanol as a white solid. 1H NMR (CDCl3) δ 1.61-1.73 (m, 3H), 2.02-2.14 (m, 1H), 2.29-2.42 (m, 2H), 2.50 (s, 6H), 3.19 (s, 3H), 3.65 (s, 2H), 4.03 (d, 2H, J=10.8 Hz), 4.17 (s, 2H), 4.35 (s, 2H), 5.09 (br s, 1H), 6.63 (d, 1H, J=7.5 Hz), 6.74 (d, 1H, J=7.5 Hz), 6.82-6.86 (m, 3H), 7.23 (d, 2H, J=7.2 Hz), 8.22 (d, 2H, J=3.6 Hz); 13C NMR (CDCl3) δ 19.44, 25.66, 30.06, 54.39, 57.89, 62.89, 67.47, 74.45, 122.08, 126.07, 128.95, 129.20, 131.76, 136.26, 138.42, 139.05, 146.82, 160.11; ES-MS m/z 432 (M+H). Anal. Calcd. For C27H33N3O2.0.6H2O: C, 73.31; H, 7.79; N, 9.50. Found: C, 73.20; H, 7.60; N, 9.36.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 hours
  3. extractionextracted with CH2Cl2 (5×15 mL)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. concentrationconcentrated
  6. customPurification of the crude material by radial chromatography on silica gel (1 mm plate, 20:1:1 CH2Cl2—CH3OH—NH4OH)

Sources & evidence

ORD record
ord-5e4c91fe6c45461bbaed8295e87d7c13
Source dataset
uspto-grants-2009_06
Patent number
US07550484B2

Reaction notes

Loading…