Diisopropylamine → HCID 58478433, compound

HRID 1027389Notes

Reaction equation

C(NC(C)C)(C)C.[Li][CH2:9][CH2:10][CH2:11][CH3:12].[C:13]([N:20]1[CH2:25][CH2:24][CH:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:22][CH2:21]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]>C1COCC1>[CH2:29]([O:28][C:26]([C:23]1([CH2:12][CH2:11][CH:10]=[CH2:9])[CH2:24][CH2:25][N:20]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:21][CH2:22]1)=[O:27])[CH3:30]

Participants

Conditions

Temperature: -78 °C

Procedure

A mixture of THF (160 mL) and diisopropyl amine (9.92 mL, 70.8 mmol, 1.2 eq) was cooled to −78° C. and a 2.5 M solution of n-BuLi in heptanes (28.3 mL, 70.8 mmol, 1.2 equiv.) was added slowly. The solution was stirred for 15 min, warmed to 0° C. for 20 min and cooled back to −78° C. Ethyl N-Boc-piperidine-4-carboxylate (11 mL, 59 mmol, 1 eq.) in 10 mL of THF was added drop-wise and stirred for 40 min before it was warmed to rt. The reaction mixture was stirred for 12 h, transferred to a separatory funnel, quenched with 500 mL of water and extracted with ethyl acetate (2×300 mL). The combined organics were dried over Na2SO4 and concentrated under vacuum to give the title compound as an yellow oil (13.9 g, 76%).

Workup

temperaturewarmed to 0° C. for 20 min
temperaturecooled back to −78° C
stirringstirred for 40 min before it
temperaturewas warmed to rt
stirringThe reaction mixture was stirred for 12 h
customtransferred to a separatory funnel
customquenched with 500 mL of water
extractionextracted with ethyl acetate (2×300 mL)
dry with materialThe combined organics were dried over Na2SO4
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-2754995ed8334e639ea70309baf8a791
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735385B2

Reaction notes

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