N1,N1,N2-trimethyl-N2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethane-1,2-diamine → (S)-N,N-dimethyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrrolidin-3-amine

HRID 447323Notes

Reaction equation

HRID 447323 reaction equation
[CH3:1][N:2]([CH3:22])[CH2:3][CH2:4][N:5]([CH3:21])[C:6]1[CH:11]=[CH:10][C:9]([B:12]2[O:16][C:15]([CH3:18])([CH3:17])[C:14]([CH3:20])([CH3:19])[O:13]2)=[CH:8][CH:7]=1.I[C:24]1C=CC(N2CC[C@H](N(C)C)C2)=CC=1>>[CH3:1][N:2]([CH3:22])[C@H:3]1[CH2:24][CH2:21][N:5]([C:6]2[CH:7]=[CH:8][C:9]([B:12]3[O:16][C:15]([CH3:17])([CH3:18])[C:14]([CH3:20])([CH3:19])[O:13]3)=[CH:10][CH:11]=2)[CH2:4]1

Participants

3

Reactant 2

HCID 58486170N1,N1,N2-trimethyl-N2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethane-1,2-diamineHCID 67446344(S)-1-(4-iodophenyl)-N,N-dimethylpyrrolidin-3-amine

Product 1

HCID 58486215(S)-N,N-dimethyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrrolidin-3-amine

Procedure

The title compound was synthesized according to the synthesis of N,N,N′-trimethyl-N′-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethane-1,2-diamine, except substituting (S)-1-(4-iodophenyl)-N,N-dimethylpyrrolidin-3-amine (500 mg, 1.58 mmol). The title compound was purified by silica gel chromatography (MeOH/CH2Cl2, 5:95 to 15:85) followed by passing a solution of the desired product (20 mL MeOH) through a PoraPak Rxn CX ionic exchange column as a yellow solid (125 mg, 25%). 1H NMR and LCMS were identical to the enantiomer, (R)—N,N-dimethyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrrolidin-3-amine.

Workup

  1. customThe title compound was purified by silica gel chromatography (MeOH/CH2Cl2, 5:95 to 15:85)

Sources & evidence

ORD record
ord-8330cc30b4874a7686e83948210c8b83
Source dataset
uspto-grants-2013_07
Patent number
US08481533B2

Reaction notes

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