1-O-tert-butyl 4-O-methyl 4-[(2E)-2-tert-butylsulfinyliminoethyl]piperidine-1,4-dicarboxylate → Tert-butyl 2-(tert-butylsulfinyl)-1-oxo-3-phenyl-2,8-diazaspiro[4.5]decane-8-carboxylate

HRID 1442905Notes

Reaction equation

[C:1]([S:5](/[N:7]=[CH:8]/[CH2:9][C:10]1([C:23](OC)=[O:24])[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1)=[O:6])([CH3:4])([CH3:3])[CH3:2].[C:27]1([Li])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CCOCC>[C:1]([S:5]([N:7]1[CH:8]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:9][C:10]2([CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[CH2:14][CH2:15]2)[C:23]1=[O:24])=[O:6])([CH3:2])([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To a −78° C. solution of 1-tert-butyl 4-methyl 4-{(2E)-2-[(tert-butylsulfinyl)imino]ethyl}piperidine-1,4-dicarboxylate (358 mg, 0.921 mmol) in ether (10 mL) was added phenyllithium (1.8 M, 1.6 mL, 3.1 mmol). The reaction was warmed to 0° C. After 1 h the reaction was quenched by the addition of saturated aqueous ammonium chloride and extracted with dichloromethane (3×). The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of 2 to 55% ethyl acetate:hexanes to give the title compound (50 mg). MS: m/z=435.2 (M+1).

Workup

customAfter 1 h the reaction was quenched by the addition of saturated aqueous ammonium chloride
extractionextracted with dichloromethane (3×)
dry with materialThe combined organic layers were dried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude product was purified by silica gel chromatography
washeluting with a gradient of 2 to 55% ethyl acetate

Sources & evidence

ORD record: ord-fa1e616c206b4699a85cc88a733aeef5
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07659264B2

Reaction notes

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