Aluminium lithium hydride → HCID 59030571, compound

HRID 1619198Notes

Reaction equation

C[O:2][C:3]([C:5]1([C:15]2[N:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:14][CH2:13][C:8]2([O:12][CH2:11][CH2:10][O:9]2)[CH2:7][CH2:6]1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[N:16]1[CH:17]=[CH:18][CH:19]=[N:20][C:15]=1[C:5]1([CH2:3][OH:2])[CH2:14][CH2:13][C:8]2([O:12][CH2:11][CH2:10][O:9]2)[CH2:7][CH2:6]1

Participants

Conditions

Temperature: -45 °C

Procedure

To a solution of 8-pyrimidin-2-yl-1,4-dioxa-spiro[4,5]decane-8-carboxylic acid methyl ester (1.02 g, 3.67 mmol) in THF (15 mL) was added LAH (1.0 M in Et2O, 3.67 ml, 3.67 mmol) dropwisely at −45° C. for 10 min. After being stirred at −45° C. for 3 h, the reaction was quenched by adding H2O (150 μL), 15% aqueous NaOH (150 μL), and H2O (450 μL) successively and stirred at 25° C. for 1 h. The resulting inorganic gel was removed by filtration and the filter cake was rinsed with EtOAc. The combined filtrates were then concentrated under reduced pressure and purification of the residue by flash chromatography (SiO2, 90-100% EtOAc/Hexanes, gradient elution) gave (8-pyrimidin-2-yl-1,4-dioxa-spiro[4,5]dec-8-yl)-methanol (518 mg, 2.07 mmol, 56%) as a colorless liquid.

Workup

customthe reaction was quenched
additionby adding H2O (150 μL), 15% aqueous NaOH (150 μL), and H2O (450 μL) successively
stirringstirred at 25° C. for 1 h
customThe resulting inorganic gel was removed by filtration
washthe filter cake was rinsed with EtOAc
concentrationThe combined filtrates were then concentrated under reduced pressure and purification of the residue by flash chromatography (SiO2, 90-100% EtOAc/Hexanes, gradient elution)

Sources & evidence

ORD record: ord-a5d1165a9279459dbdc408ba4350e792
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772296B2

Reaction notes

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