HCID 11300027, compound → 1-(4-Benzyl-morpholin-2-yl)-2-methyl-propan-1-ol

HRID 131190Notes

Reaction equation

[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH:14]([OH:18])[CH:15]([CH3:17])[CH3:16])[C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH:14]([OH:18])[CH:15]([CH3:16])[CH3:17])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred solution of 53 (1.97 g, 7.47 mmol) in tetrahydrofuran (50 ml) at room temperature under nitrogen was added borane-tetrahydrofuran complex (30 ml of a 1M solution, ca 4 eq.). The reaction was heated to 60° C. and followed by TLC-analysis. When all starting material had been consumed a few drops of methanol were added followed by a similar amount of 1N hydrochloric acid and heating was continued for another hour. Organic solvents were removed in vacuo and the remaining solution was poured onto 1M potassium carbonate solution (30 ml), extracted with diethyl ether. The organic layers were dried over magnesium sulphate and purified by column chromatography (gradient from 15% ethyl acetate in hexane [v/v]) gave 54 (1.8 g, 97%). MW 249.36; C15H23NO2; LCMS (6 min method): m/z 250 [M+H]+; RT=0.838.

Workup

customWhen all starting material had been consumed a few drops of methanol
additionwere added
temperatureheating
waitwas continued for another hour
customOrganic solvents were removed in vacuo
additionthe remaining solution was poured onto 1M potassium carbonate solution (30 ml)
extractionextracted with diethyl ether
dry with materialThe organic layers were dried over magnesium sulphate
custompurified by column chromatography (gradient from 15% ethyl acetate in hexane [v/v])

Sources & evidence

ORD record: ord-778c50090c0341a3ad706c8e713d3e39
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07384941B2

Reaction notes

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