Diisopropylamine → HCID 117723631, compound

HRID 1747278Notes

Reaction equation

C(NC(C)C)(C)C.[Li]CCCC.[F:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1.[C:20]([N:27]1[CH2:32][CH2:31][CH:30]([CH:33]=[O:34])[CH2:29][CH2:28]1)([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]>C1COCC1>[F:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][C:19]=1[CH:33]([OH:34])[CH:30]1[CH2:31][CH2:32][N:27]([C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[CH2:28][CH2:29]1

Participants

Conditions

Temperature: 0 °C

Procedure

Diisopropylamine (0.66 ml, 4.69 mmol) was dissolved in THF (30 ml) and cooled to −78° C. nBuLi (2.13 ml, 2.20 M in cyclohexane, 4.69 mmol) was added drop-wise and the reaction mixture was stirred at −78° C. for 10 min, at 0° C. for 30 min, and re-cooled to −78° C. 3-Fluoro-pyridine (0.40 ml, 4.69 mmol) was added drop-wise over 5 min, and the reaction mixture was stirred for 45 min. A solution of N-Boc-4-piperidinecarboxaldehyde (1.00 g, 4.69 mmol) in THF (10 ml) was added and the reaction mixture was warmed to RT and stirred for 15 min. The reaction mixture was quenched with sat aq NH4OAc (10 mL), diluted with EtOAc (100 mL), washed with water (2×50 mL), dried (MgSO4) and concentrated in vacuo to give the title compound as an orange oil (1.42 g, 98%). LCMS (ES+): 255.0 [MH-t-Bu]+.

Workup

additionwas added drop-wise
temperaturere-cooled to −78° C
stirringthe reaction mixture was stirred for 45 min
temperaturethe reaction mixture was warmed to RT
stirringstirred for 15 min
customThe reaction mixture was quenched with sat aq NH4OAc (10 mL)
additiondiluted with EtOAc (100 mL)
washwashed with water (2×50 mL)
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-51810d6a63044990a47af649ac25c354
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150574B2

Reaction notes

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