Water → 1,1-Dimethylethyl (1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]-3-hydroxypropyl}-4-piperidinyl)carbamate

HRID 15313Notes

Reaction equation

[CH3:1][C:2]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH:16]([C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[C:28]([O:31][CH3:32])[N:29]=3)[N:24]=[CH:23][C:22]=2[F:33])[C:17](OC)=[O:18])[CH2:11][CH2:10]1)=[O:7])([CH3:4])[CH3:3].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[F:33][C:22]1[CH:23]=[N:24][C:25]2[C:30]([C:21]=1[CH:16]([CH2:17][OH:18])[CH2:15][N:12]1[CH2:11][CH2:10][CH:9]([NH:8][C:6](=[O:7])[O:5][C:2]([CH3:3])([CH3:4])[CH3:1])[CH2:14][CH2:13]1)=[N:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2

Participants

Conditions

Temperature: -10 °C

Procedure

A solution of methyl 3-[4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-1-piperidinyl]-2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]propanoate (26.63 g, containing about 9% DMF by weight, estimate 52.5 mmol) was stirred under argon at −70° C. and treated with a 1M solution of lithium aluminium hydride in THF (60 ml). The mixture was allowed to warm to −10° C., stirred in an ice bath for 2 hours, treated with water (4.5 ml), 2N NaOH solution (8.44 ml) and water (9.7 ml) and stirred a further 30 minutes. The solid was filtered off and washed with THF and the filtrate evaporated. Chromatography of the residue (methanol/dichloromethane gradient) gave the product (18.28 g).

Workup

stirringstirred a further 30 minutes
filtrationThe solid was filtered off
washwashed with THF
customthe filtrate evaporated

Sources & evidence

ORD record: ord-924d49eebc32441b81740272ae48ad5b
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732461B2

Reaction notes

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