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Lithium borohydride → [3-Amino-4-(3,3''-dimethyl-3',4',5',6'-tetrahydro-2'H-[2,2':6',2'']terpyridin-1'-ylmethyl)-phenyl]-methanol

HRID 1987358
Notes
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Reaction equation

HRID 1987358 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[CH:16]([C:17]3[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][N:18]=3)[CH2:15][CH2:14][CH2:13][CH:12]2[C:24]2[C:29]([CH3:30])=[CH:28][CH:27]=[CH:26][N:25]=2)=[C:6]([NH2:31])[CH:5]=1.[Li+].[BH4-]>C1COCC1.[OH-].[Na+]>[NH2:31][C:6]1[CH:5]=[C:4]([CH2:3][OH:2])[CH:9]=[CH:8][C:7]=1[CH2:10][N:11]1[CH:12]([C:24]2[C:29]([CH3:30])=[CH:28][CH:27]=[CH:26][N:25]=2)[CH2:13][CH2:14][CH2:15][CH:16]1[C:17]1[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][N:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 674211763-amino-4-(3,3''-dimethyl-3',4',5',6'-tetrahydro-2'H-[2,2'; 6',2'']terpyridin-1'-ylmethyl)-benzoic acid methyl ester

Product 1

HCID 67421957[3-Amino-4-(3,3''-dimethyl-3',4',5',6'-tetrahydro-2'H-[2,2':6',2'']terpyridin-1'-ylmethyl)-phenyl]-methanolYield 38.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent
HCID 14798
Sodium Hydroxide
Solvent

Procedure

To a solution of 3-amino-4-(3,3″-dimethyl-3′,4′,5′,6′-tetrahydro-2′H-[2,2′;6′,2″]terpyridin-1′-ylmethyl)-benzoic acid methyl ester (0.61 g, 1.42 mmol) in THF (14 mL) was added LiBH4 (430 mg, 19.74 mmol) and the mixture was heated to reflux overnight. The mixture was cooled to room temperature, diluted with 1.0 N NaOH (20 mL) and extracted with CH2Cl2 (5×30 mL). The combined organic extracts were dried (Na2SO4) and concentrated. Purification of the crude material by radial chromatography on silica gel (2 mm plate, 20:1:1 CH2Cl2—CH3OH—NH4OH) provided 0.220 g (37%) of COMPOUND 59 as a white solid. 1H NMR (CDCl3) δ 1.23 (br s, 1H), 1.47-1.72 (m, 3H), 1.88-1.95 (m, 1H), 2.04-2.18 (m, 2H), 2.35 (s, 6H), 3.32 (s, 2H), 3.73 (dd, 2H, J=11.7, 3.0 Hz), 4.26 (d, 2H, J=3.3 Hz), 4.53 (br s, 2H), 6.03 (s, 1H), 6.07 (d, 1H, J=7.8 Hz), 6.48 (d, 1H, J=7.2 Hz), 6.86 (dd, 2H, J=7.8, 4.8 Hz), 7.15 (d, 2H, J=7.5 Hz), 8.33 (d, 2H, J=3.9 Hz). 13C NMR (CDCl3) δ 19.44, 25.02, 32.92, 60.69, 65.60, 68.25, 112.98, 115.09, 122.09, 122.80, 129.96, 131.38, 138.18, 140.42, 146.89, 147.51, 161.18; ES-MS m/z 403 (M+H). Anal. Calcd. For C25H30N4O.1.0H2O: C, 71.40; H, 7.67; N, 13.32. Found: C, 71.31; H, 7.55; N, 13.22.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux overnight
  3. extractionextracted with CH2Cl2 (5×30 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 (2 mm plate, 20:1:1 CH2Cl2—CH3OH—NH4OH)

Sources & evidence

ORD record
ord-b227d6cd32f047fdbe9e84a267f5725a
Source dataset
uspto-grants-2009_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07550484B2

Reaction notes

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