Aluminium lithium hydride → HCID 117914461, compound

HRID 526818Notes

Reaction equation

[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:22][CH2:23][CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[C:8]([O:11][CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH:9]=2)[CH2:4][O:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[OH:3][CH2:4][C:5]1[C:10]([CH2:2][OH:1])=[CH:9][C:8]([O:11][CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:20])[CH3:18])=[C:7]([O:22][CH2:23][CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of compound 26 (5.00 g, 11.0 mmol) in THF (50 mL) was charged with lithium aluminum hydride (1 M solution in diethyl ether, 33.2 mL, 33.2 mmol) at 0° C. The resulting reaction mixture was stirred at 0° C. for 1 h and quenched with ice-cold water at 0° C. The reaction mixture was diluted with chloroform (300 mL) and filtered through a Celite pad, and the Celite pad was washed with chloroform (2×300 ml). The filtrate was concentrated under vacuum to afford 27 (4.50 g, 90%) as a colorless gum: 1H NMR (400 MHz, DMSO-d6) δ 6.99 (s, 2H), 6.90 (t, J=5.9 Hz, 2H), 4.97 (brs, 2H), 4.44 (s, 4H), 3.92 (t, J=5.6 Hz, 4H), 3.30-3.22 (m, 4H), 1.38 (s, 18H).

Workup

customThe resulting reaction mixture
customquenched with ice-cold water at 0° C
additionThe reaction mixture was diluted with chloroform (300 mL)
filtrationfiltered through a Celite pad
washthe Celite pad was washed with chloroform (2×300 ml)
concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record: ord-9cdb36396fca4f73abbffac322927bc2
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346753B2

Reaction notes

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