Sodium triacetoxyborohydride → (1H-Benzoimidazol-2-ylmethyl)-(4-{[(pyrrolidin-2-ylmethyl)-amino]-methyl}-benzyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine

HRID 7173

Reaction equation

HRID 7173 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][CH2:12][C@@H:9]1[CH:10]=O)=O)(C)(C)C.[NH:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[C:16]1[CH2:24][N:25]([CH:35]1[C:44]2[N:43]=[CH:42][CH:41]=[CH:40][C:39]=2[CH2:38][CH2:37][CH2:36]1)[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][NH2:34])=[CH:29][CH:28]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[NH:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[C:16]1[CH2:24][N:25]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][NH:34][CH2:10][CH:9]2[CH2:12][CH2:13][CH2:14][NH:8]2)=[CH:29][CH:28]=1)[CH:35]1[C:44]2[N:43]=[CH:42][CH:41]=[CH:40][C:39]=2[CH2:38][CH2:37][CH2:36]1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 7009153N-(tert-Butoxycarbonyl)-D-prolinalHCID 21985008N-[(1H-Benzo[d]imidazol-2-yl)methyl]-N-(4-(aminomethyl)-benzyl)-5,6,7,8-tetrahydroquinolin-8-amine

Product 1

HCID 22018599(1H-Benzoimidazol-2-ylmethyl)-(4-{[(pyrrolidin-2-ylmethyl)-amino]-methyl}-benzyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using General Procedure B: To a stirred solution of N-(tert-butoxycarbonyl)-D-prolinal (0.121 g, 0.61 mmol) in dry CH2Cl2 (9 mL) was added N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (0.236 g, 0.59 mmol) at room temperature and the mixture stirred for 40 min. To the resultant mixture was added sodium triacetoxyborohydride (0.174 g, 0.82 mmol) and the mixture stirred overnight at room temperature. Purification and separation of the crude material by radial chromatography on a 2 mm TLC grade silica gel plate (CH2Cl2/MeOH/NH4OH, 50:1:1) afforded the more polar mono-alkylated (77 mg, 23%) and the less polar dialkylated (70 mg, 21%) products, both as white foams.

Workup

  1. stirringthe mixture stirred overnight at room temperature
  2. customPurification and separation of the crude material by radial chromatography on a 2 mm TLC grade silica gel plate (CH2Cl2/MeOH/NH4OH, 50:1:1)
  3. customafforded the more polar mono-alkylated (77 mg, 23%)

Sources & evidence

ORD record
ord-f60b003fd2d94e8d9b9542ea7a90f1dd
Source dataset
uspto-grants-2006_08
Patent number
US07084155B2

Linked notes

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