Water → tert-Butyl (4-(2-hydroxyethyl)pyridin-2-yl)carbamate

HRID 2069026Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[C:13]([CH2:15][C:16](OCC)=[O:17])[CH:12]=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C[AlH]CC(C)C)C.O>C1COCC1>[OH:17][CH2:16][CH2:15][C:13]1[CH:12]=[CH:11][N:10]=[C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH:14]=1

Participants

Conditions

Temperature: -69 °C

Procedure

To a solution of ethyl 2-(2-(tert-butoxycarbonylamino)pyridin-4-yl)acetate (19) (WO 2007089512) (10.0 g, 35.7 mmol) under nitrogen in THF (100 mL), at −78° C., was added DIBAL (1M solution in THF, 71.3 mL, 71.3 mmol) over 1 hr. The reaction mixture was stirred at −78 to −60° C. for 40 min and then warmed to −15° C. over 1 hr. The solution was re-cooled to −78° C. and treated with further DIBAL (1M solution in THF, 35 mL, 35.7 mmol). The mixture was allowed to warm to −40° C. and stirred for 1 hr. Water (10 mL) was added cautiously to quench the reaction followed by MgSO4 (20 g) and the solids removed by filtration. The filtrate was evaporated to dryness in vacuo and the residue subjected to column chromatography (SiO2, 330 g, 65% EtOAc in hexanes) to give the title compound (20) (6.00 g, 64%) as a yellow solid: m/z 239 (M+H)+ (ES+).

Workup

temperaturewarmed to −15° C. over 1 hr
temperatureThe solution was re-cooled to −78° C.
temperatureto warm to −40° C.
stirringstirred for 1 hr
customto quench the reaction
customthe solids removed by filtration
customThe filtrate was evaporated to dryness in vacuo

Sources & evidence

ORD record: ord-f621b5cb181f4af7a74524ebac6fce7f
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299073B2

Reaction notes

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