Sodium Hydroxide → HCID 45139977, compound

HRID 574281Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][CH:15]([N:19]([CH2:29][CH2:30][CH3:31])[C:20](=O)[CH2:21][N:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[CH2:16]2)=[CH:11][CH:10]=1.[OH-].[Na+]>C1COCC1>[CH3:7][O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][CH:15]([N:19]([CH2:20][CH2:21][N:22]3[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]3)[CH2:29][CH2:30][CH3:31])[CH2:16]2)=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of LiAlH4 (1.735 g, 45.73 mmol) in THF (100 ml) at 0° C. was added 7a (3.16 g, 9.15 mmol) in a solution of THF (25 ml). After addition, the mixture was refluxed for 2 h and cooled to 0° C. 15% NaOH was added dropwise to quench the reaction and deactivate the LiAlH4, and the mixture stirred for 20 min, and filtered, washed with ethyl acetate. The solution was dried over Na2SO4, filtered, and concentrated. This crude product was then purified through column chromatography using 20% MeOH in ethyl acetate to get 8a as transparent thick liquid (2.23 g, 74%). 1H NMR (400 MHz, CDCl3) δ ppm 0.91-0.96 (t, 3H, J=10 Hz), 1.40-1.6 (m, 3H), 1.97-2.01 (m, 1H), 2.139 (bs, 1H) 2.41-3.11 (m, 18H), 3.82 (s, 3H), 6.61 (s, 1H), 6.66-6.79 (d, 1H, J=6 Hz), 6.95-6.98 (d, 1H, J=8.8 Hz).

Workup

additionAfter addition
temperaturethe mixture was refluxed for 2 h
customto quench
customthe reaction
filtrationfiltered
washwashed with ethyl acetate
dry with materialThe solution was dried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThis crude product was then purified through column chromatography

Sources & evidence

ORD record: ord-d84b3384e0a248ff9d10c1f148c69480
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034877B2

Reaction notes

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