Dichloromethane → HCID 69296792, compound

HRID 1624232Notes

Reaction equation

HRID 1624232 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-1bd9df8674e6425f941df6c171ecb2e8
Source dataset
uspto-grants-2014_07
Patent number
US08778967B2

Reaction notes

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