Borane;tetrahydrofuran → 2-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butan-1-amine

HRID 1853914Notes

Reaction equation

[CH3:1][C:2]1([CH3:20])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([CH:15]([CH2:18][CH3:19])[C:16]#[N:17])=[CH:11][CH:10]=2)[O:3]1.B.C1COCC1>>[CH3:7][C:6]1([CH3:8])[C:2]([CH3:1])([CH3:20])[O:3][B:4]([C:9]2[CH:14]=[CH:13][C:12]([CH:15]([CH2:18][CH3:19])[CH2:16][NH2:17])=[CH:11][CH:10]=2)[O:5]1

Participants

Reactant 2

HCID 2723981Borane;tetrahydrofuran

HCID 674495172-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butanenitrile

Product 1

HCID 674518552-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butan-1-amineYield 93%

Procedure

Following the procedure outlined for Example 666, 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butanenitrile (3.4 g, 12.5 mmol) was reacted with BH3.THF (1.0 M in THF, 64 mL, 64 mmol) to afford the desired product (3.2 g, 93%) as light yellow oil: ESI MS m/z 276 [C16H26BNO2+H]+.

Sources & evidence

ORD record: ord-bb73fd5ec4e14499bb71d149aeb401b4
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962648B2

Reaction notes

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