Aluminium lithium hydride → HCID 57794732, compound

HRID 2099270Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([C@@:13]2([C:25]#[N:26])[CH2:15][C@H:14]2[CH2:16][O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(OCC)C>[C:7]1([C@@:13]2([CH2:25][NH2:26])[CH2:15][C@H:14]2[CH2:16][O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To 19.4 mL IM lithium aluminum hydride (19.4 mmol) in diethyl ether at 0° C. was added (1R,2R)-1-phenyl-2-{[(phenylmethyl)oxy]methyl}cyclopropanecarbonitrile (5.10 g, 19.4 mmol), accessed via the method of Preparation 3B, dissolved in 20 mL diethyl ether. After complete addition, the reaction mixture was stirred at 0° C. for 3 h. The reaction mixture was diluted with 360 mL diethyl ether and quenched with successive addition of 0.6 mL water, 0.6 mL 15% NaOH, and 3.0 mL water. The reaction mixture was filtered and the filtrate was concentrated to a clear oil. The oil was purified by flash chromatography (SiO2, 3→7% CH3OH/EtOAc with 1% NH4OH) to give the title product (3.03 g, 11.3 mmol, 59%) as a single diastereomer. 1H NMR (300 MHz, CDCl3) δ 7.35-7.21 (m, 10H), 4.35-4.25 (m, 2H), 3.22-3.18 (m, 1H), 3.00-2.94 (m, 2H), 2.43 (d, J=13.5 Hz, 1H), 1.36 (m, 1H), 0.91 (m, 1H), 0.78 (m, 1H). ES-LCMS m/z 268.4 (M+H).

Workup

additionAfter complete addition
customquenched with successive addition of 0.6 mL water, 0.6 mL 15% NaOH, and 3.0 mL water
filtrationThe reaction mixture was filtered
concentrationthe filtrate was concentrated to a clear oil
customThe oil was purified by flash chromatography (SiO2, 3→7% CH3OH/EtOAc with 1% NH4OH)

Sources & evidence

ORD record: ord-641d78c87f854707b17ea821a7692072
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07569579B2

Reaction notes

Loading…