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

HRID 447321Notes

Reaction equation

HRID 447321 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 66730449(R)-1-(4-iodophenyl)-N,N-dimethylpyrrolidin-3-amine

Product 1

HCID 58486284(R)-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, substituting (R)-1-(4-iodophenyl)-N,N-dimethylpyrrolidin-3-amine (300 mg, 0.95 mmol). The title compound was purified by silica gel chromatography (MeOH/CH2Cl2, 2:98 to 12:88) as a yellow solid (95 mg, 32%). 1H NMR (400 MHz, MeOD) δ 7.58 (d, J=7.6 Hz, 2H), 6.52 (d, J=7.8 Hz, 2H), 3.55-3.51 (m, 1H), 3.48-3.43 (m, 1H), 3.32-3.26 (m, 1H), 3.15-3.11 (m, 1H), 2.92-2.86 (m, 1H), 2.55 (s, 3H), 2.32 (s, 6H), 2.28-2.22 (m, 1H), 1.94-1.86 (m, 1H); MS ESI 317.2 [M+H]+, calcd for [C18H29BN2O2+H]+ 317.23.

Workup

  1. customThe title compound was purified by silica gel chromatography (MeOH/CH2Cl2, 2:98 to 12:88) as a yellow solid (95 mg, 32%)

Sources & evidence

ORD record
ord-8fda33f463a94b4f9644a6a1d08c1da6
Source dataset
uspto-grants-2013_07
Patent number
US08481533B2

Reaction notes

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