Diisopropylamine → Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylate

HRID 395863Notes

Reaction equation

C(NC(C)C)(C)C.[Li]CCCC.[C:13]([N:20]1[CH2:25][CH2:24][C:23](=[O:26])[CH2:22][CH2:21]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].C1(N[S:34]([C:37]([F:40])([F:39])[F:38])(=[O:36])=[O:35])C=CC=CC=1>C1COCC1>[C:13]([N:20]1[CH2:25][CH2:24][C:23]([O:26][S:34]([C:37]([F:40])([F:39])[F:38])(=[O:36])=[O:35])=[CH:22][CH2:21]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]

Participants

Conditions

Temperature: -78 °C

Procedure

To a stirring solution of diisopropylamine (38.7 mL, 275 mmol) in THF (900 mL) at 0° C. was added dropwise via an addition funnel a solution of n-BuLi in hexanes (1.6 MN 171.5 mL, 276 mmol). After 25 min, the solution was cooled to −78° C. To this solution was added dropwise via an addition funnel a solution of 1-Boc-4-piperidinone (50 g, 250.9 mmol) in THF (300 mL). After 30 min, a solution of N-phenyltrifluoromethanesulfonamide (95.9 g, 268.5 mmol) in THF (300 mL) was added and the solution was warmed to 0° C. After 3 h, the solvents were evaporated in vacuo and the residue was loaded into a silica gel column with a minimal amount of dichloromethane and eluted with 5% ethyl acetate/hexanes. The product containing fractions were combined and concentrated in vacuo to give 74.84 g (90%) of a light yellow oil.

Workup

waitAfter 30 min
temperaturethe solution was warmed to 0° C
waitAfter 3 h
customthe solvents were evaporated in vacuo
washeluted with 5% ethyl acetate/hexanes
additionThe product containing fractions
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-8fee19067acd4c0eb57319afd0e1dd2d
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06605626B2

Reaction notes

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