Sodium Chloride → (S)-tert-butyl 1-oxohexan-2-ylcarbamate

HRID 1182285Notes

Reaction equation

[H-].COCCO[Al+]OCCOC.CON(C)[C:16]([C@@H:18]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:19][CH2:20][CH2:21][CH3:22])=[O:17].[Cl-].[Na+]>C1(C)C=CC=CC=1>[CH:16]([C@@H:18]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:19][CH2:20][CH2:21][CH3:22])=[O:17]

Participants

Conditions

Temperature: -20 °C

Procedure

To a stirred solution of 54.0 mL (180.0 mmol) of 65 wt % bis (2-methoxyethoxy) aluminum hydride in toluene in 100 mL of toluene at −20° C. was added a solution of 35.0 g (120.0 mmol) of tert-butyl (1S)-1-{[methoxy(methyl)amino]carbonyl}pentylcarbamate in 100 mL of toluene over 30 min. After stirring at −20° C. for 2 h, 300 mL of 3M aqueous sodium chloride was added dropwise, and the layers were separated. The toluene portion was washed with 100 mL of 1 N hydrochloric acid (2×), 50 mL of 0.1 N sodium hydroxide (2×), 50 mL of brine, dried over anhydrous magnesium sulfate, and then concentrated to 200 mL. The aldehyde solution was used immediately. An aliquot was removed and concentrated, and the aldehyde was analyzed immediately. 1H-NMR (400 MHz, DMSO-d6): δ 9.39 (s, 1H), 7.23 (d, J=7 Hz, 1H), 3.75 (m, 1H), 1.70–1.08 (m, 6H), 1.36 (s, 9H), 0.81 (t, J=6 Hz, 3H).

Workup

customthe layers were separated
washThe toluene portion was washed with 100 mL of 1 N hydrochloric acid (2×), 50 mL of 0.1 N sodium hydroxide (2×), 50 mL of brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated to 200 mL
customAn aliquot was removed
concentrationconcentrated

Sources & evidence

ORD record: ord-ea6fa95d8f8c49c98ffdc6235ef50d0e
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07288541B2

Reaction notes

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