Dimethylamine → [1-(2-Fluoro-4-nitro-phenyl)-pyrrolidin-2-ylmethyl]-dimethyl-amine

HRID 2236511Notes

Reaction equation

HRID 2236511 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[CH:16]=O.[CH3:18][NH:19][CH3:20].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[CH2:16][N:19]([CH3:20])[CH3:18]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 593003601-(2-Fluoro-4-nitro-phenyl)-pyrrolidine-2-carbaldehyde

Product 1

HCID 59300313[1-(2-Fluoro-4-nitro-phenyl)-pyrrolidin-2-ylmethyl]-dimethyl-amineYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(2-Fluoro-4-nitro-phenyl)-pyrrolidine-2-carbaldehyde (100 mg, 0.42 mmol) and dimethylamine (large excess) is stirred at room temperature in CH2Cl2 for 5 min and NaBH(OAc)3 (120 mg, 0.57 mmol) is added. The reaction is stopped after 30 min as TLC suggested complete conversion and the desired product (77 mg, 69%) is isolated after chromatography.

Sources & evidence

ORD record
ord-b2bba44e5e5b409faf366d48089cc8eb
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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