Dichloromethane → HCID 69296792, compound

HRID 899584Notes

Reaction equation

HRID 899584 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][NH:11][CH:12]1[C:21]2[N:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH2:15][CH2:14][CH2:13]1.[C:22]([O:26]C([N:29]1[CH2:35][CH2:34][CH2:33][C@H:30]1[CH:31]=O)=O)(C)(C)C.[BH-](OC(C)=O)(OC(C)=O)[O:37]C(C)=O.[Na+].[CH2:50]([Cl:52])[Cl:51]>>[CH2:50]([Cl:52])[Cl:51].[CH3:22][OH:26].[NH4+:1].[OH-:37].[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][N:11]([CH2:31][CH:30]1[CH2:33][CH2:34][CH2:35][NH:29]1)[C@@H:12]1[C:21]2[N:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH2:15][CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 2734674tert-butyl (2S)-2-formylpyrrolidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 21985053HCID 21985053, compound

Product 2

HCID 21896990Dichloromethane methanol ammonium hydroxideHCID 69296792HCID 69296792, compoundYield 30%

Procedure

Using General Procedure B: To a stirred solution of (1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (148 mg, 0.53 mmol) and N-tert-butoxycarbonyl-L-prolinal (110 mg, 0.55 mmol) in CH2Cl2 (5 mL) was added NaBH(OAc)3 (146 mg, 0.69 mmol) and the resultant mixture was stirred at room temperature overnight. Purification of the crude material by radial chromatography on silica gel gel (2 mm plate, 50:1:1 CH2Cl2/MeOH/NH4OH then 10:1:1 CH2Cl2/MeOH/NH4OH) afforded the desired amine (73 mg, 30%) as a yellow oil.

Workup

  1. customPurification of the crude material by radial chromatography on silica gel gel (2 mm plate, 50:1:1 CH2Cl2/MeOH/NH4OH

Sources & evidence

ORD record
ord-c89663fd66924e66a1199401cee4ffe3
Source dataset
uspto-grants-2008_04
Patent number
US07354932B2

Reaction notes

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