Aluminium lithium hydride → (3-(8-(1,3-Dioxolan-2-yl)octyloxy)phenyl)(phenyl)methanamine

HRID 332649Notes

Reaction equation

[N:1]([CH:4]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:5]1[CH:6]=[C:7]([CH:22]=[CH:23][CH:24]=1)[O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]1[O:21][CH2:20][CH2:19][O:18]1)=[N+]=[N-].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[O:18]1[CH2:19][CH2:20][O:21][CH:17]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][O:8][C:7]1[CH:6]=[C:5]([CH:4]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[NH2:1])[CH:24]=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 2-(8-(3-(azido(phenyl)methyl)phenoxy)octyl)-1,3-dioxolane (1.11 g, 2.71 mmol) in THF (15 mL) at −78° C. under an atmosphere of nitrogen, a solution of lithium aluminium hydride (2.0M in THF, 2.8 mL, 5.60 mmol) was added drop wise. After stirring the reaction at −78° C. for 1 hour, the reaction mixture was warmed up to 0° C. for 1 hour. The reaction mixture was quenched with water (304 mL), 2M sodium hydroxide (304 mL) and water (304 mL×3). Anhydrous magnesium sulphate and ethyl acetate were added, and the reaction mixture filtered and concentrated under reduced pressure. The crude material was purified by column chromatography eluting with 100% iso-hexane to 100% DCM to 25:1 DCM:methanol (0.63 g, 39% based on (3-(8-(1,3-dioxolan-2-yl)octyloxy)phenyl)(phenyl)methanol).

Workup

customthe reaction at −78° C. for 1 hour
customThe reaction mixture was quenched with water (304 mL), 2M sodium hydroxide (304 mL) and water (304 mL×3)
additionAnhydrous magnesium sulphate and ethyl acetate were added
filtrationthe reaction mixture filtered
concentrationconcentrated under reduced pressure
customThe crude material was purified by column chromatography
washeluting with 100% iso-hexane to 100% DCM to 25:1 DCM

Sources & evidence

ORD record: ord-b40ee59728714d03a3d5bb4c3c94ce3f
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877774B2

Reaction notes

Loading…