Sodium Chloride → (S)-tert-butyl 1-oxohexan-2-ylcarbamate
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
Procedure
To a stirred solution of bis (2-methoxyethoxy) aluminum hydride (54.0 mL, 65% by weight in toluene, 180.0 mmol) in toluene (100 mL) at −20° C. was added a solution of tert-butyl (1S)-1-{[methoxy(methyl)amino]carbonyl}pentylcarbamate (35.0 g, 120.0 mmol) in toluene (100 mL) over 30 min. After 2 h at −20° C., 3M sodium chloride (300 mL) was added dropwise, and the layers were separated. The toluene portion was washed with 1N hydrochloric acid (2×100 mL), 0.1N sodium hydroxide (2×50 mL), and brine (50 mL), dried over magnesium sulfate, and concentrated to 200 mL. The aldehyde was used immediately in solution. An aliquot of the solution 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 1N hydrochloric acid (2×100 mL), 0.1N sodium hydroxide (2×50 mL), and brine (50 mL)
- dry with materialdried over magnesium sulfate
- concentrationconcentrated to 200 mL
- customAn aliquot of the solution was removed
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-3368187d332b4263a15eb7908297efe0
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07402606B2
Reaction notes
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