Aluminium lithium hydride → (1-Benzyl-7-methylazepan-3-yl)methanol

HRID 467478Notes

Reaction equation

[CH2:1]([N:8]1[CH:14]([CH3:15])[CH2:13][CH2:12][CH2:11][CH:10]([C:16](OC)=[O:17])[C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:1]([N:8]1[CH:14]([CH3:15])[CH2:13][CH2:12][CH2:11][CH:10]([CH2:16][OH:17])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of methyl 1-benzyl-7-methyl-2-oxoazepane-3-carboxylate (2-4, 3.8 g, 14 mmol, 1.0 equiv) in THF (70 mL) at 0° C. under nitrogen was added solid lithium aluminum hydride (2.6 g, 69 mmol, 5.0 equiv) and the resulting mixture was stirred at 0° C. for 1.5 hours. Excess LAH was quenched with water (2 mL) and 15% aqueous sodium hydroxide solution (2 mL). The mixture was dried over sodium sulfate and concentrated. The residue was purified by silica gel chromatography (0-100% ethyl acetate/hexanes gradient) to yield (1-benzyl-7-methylazepan-3-yl)methanol (2-5) as a clear oil. 1H NMR (400 MHz, CDCl3) 7.36 (m, 5H), 3.68-1.49 (m, 18H). LRMS m/z (M+H) 234.3 found, 234.2 required.

Workup

customExcess LAH was quenched with water (2 mL) and 15% aqueous sodium hydroxide solution (2 mL)
dry with materialThe mixture was dried over sodium sulfate
concentrationconcentrated
customThe residue was purified by silica gel chromatography (0-100% ethyl acetate/hexanes gradient)

Sources & evidence

ORD record: ord-d06ea5300f9742e49e0c192a2cc29c4b
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08623863B2

Reaction notes

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