N-methoxy-N-methylpentanamide → 1-[2-(t-Butoxycarbonylamino)pyridin-3-yl]hexan-2-one

HRID 1769208Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C:9]1[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])(CC)C.CON(C)[C:24](=[O:29])[CH2:25][CH2:26][CH2:27][CH3:28]>O1CCCC1.CCOCC>[C:1]([O:5][C:6]([NH:8][C:9]1[C:14]([CH2:15][C:24](=[O:29])[CH2:25][CH2:26][CH2:27][CH3:28])=[CH:13][CH:12]=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: -50 °C

Procedure

A solution of 2-(t-butoxycarbonylamino)-3-methylpyridine (41) (5.3 g) (prepared, e.g, as described in Preparation 28), in tetrahydrofuran (100 ml) was cooled to -50° C. and a solution of sec-butyllithium (46 ml of 1.3M in cyclohexane) was added. After 10 minutes, the dark solution was treated with N-methoxy-N-methylvaleramide (4.4 g) and the resulting solution was stirred 10 minutes. The mixture was diluted with ether, washed with water, dried over sodium sulfate and evaporated. Crystallization of the residue from hexane afforded 1-[2-(t-butoxycarbonylamino)-pyridin-3-yl]hexan-2-one (4.3 g), a compound of Formula (42), as a white solid m.p. 66°-67° C.

Workup

washwashed with water
dry with materialdried over sodium sulfate
customevaporated
customCrystallization of the residue from hexane

Sources & evidence

ORD record: ord-4e7c4d47015044afa81c7ddb3e419502
Source dataset: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05380739

Reaction notes

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