Lauric Acid → 1-oxododecyl-3-(O-tert-butyldimethylsilyoxy)piperidine

HRID 2395713Notes

Reaction equation

[C:1]([OH:14])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C(Cl)(=O)C(Cl)=O.[Si:21]([O:28][CH:29]1[CH2:34][CH2:33][CH2:32][NH:31][CH2:30]1)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22].C(N(CC)CC)C>C(Cl)Cl.CN(C)C=O>[O:14]=[C:1]([N:31]1[CH2:32][CH2:33][CH2:34][CH:29]([O:28][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:22])[CH3:23])[CH2:30]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

Conditions

Temperature: 0 °C

Procedure

Dissolve lauric acid (0.77 g) in methylene chloride (50mL) and cool to 0° C. Add oxalyl chloride (0.37 mL) and dimethylformamide (3 drops). Allow to warm to room temperature and stir for 1 hour. Add, by dropwise addition, to a solution of 3-(O-tert-butyldimethylsilyloxy)piperidine (0.76 g, 3.5 mmol) and triethylamine (1 mL) in methylene chloride (20 mL). Stir overnight. Dilute with methylene chloride (50 mL) and separate the organic phase. Wash twice with 10% sodium hydroxide, once with 10% hydrochloric acid, and once with saturated sodium hydrogen carbonate and once with brine. Dry (Na2SO4) and evaporate the solvent in vacuo to give 1-oxododecyl-3-(O-tert-butyldimethylsilyoxy)piperidine.

Workup

temperatureAllow to warm to room temperature
stirringStir overnight
customseparate the organic phase
washWash twice with 10% sodium hydroxide, once with 10% hydrochloric acid
dry with materialDry (Na2SO4)
customevaporate the solvent in vacuo

Sources & evidence

ORD record: ord-09da1355281f47208f3af32d81f56483
Source dataset: uspto-grants-1996_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05489600

Reaction notes

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