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

HRID 1853910Notes

Reaction equation

[CH3:1][C:2]1([CH3:21])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3([C:19]#[N:20])[CH2:18][CH2:17][CH2:16]3)=[CH:11][CH:10]=2)[O:3]1.B.C1COCC1>>[CH3:7][C:6]1([CH3:8])[C:2]([CH3:1])([CH3:21])[O:3][B:4]([C:9]2[CH:10]=[CH:11][C:12]([C:15]3([CH2:19][NH2:20])[CH2:16][CH2:17][CH2:18]3)=[CH:13][CH:14]=2)[O:5]1

Participants

Reactant 2

HCID 2723981Borane;tetrahydrofuran

HCID 580346631-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutanecarbonitrile

Product 1

HCID 67452433(1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutyl)methanamineYield 92%

Procedure

Following the procedure outlined for Example 666, 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutane carbonitrile (4.0 g, 14 mmol) was reacted with BH3.THF (1.0 M in THF, 60 mL, 60 mmol) to afford the desired product (3.7 g, 91%) as a yellow oil: ESI MS m/z 288 [C11H2BNO2+H]+.

Sources & evidence

ORD record: ord-d2881fe21617426bb27b17e6c6776973
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962648B2

Reaction notes

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