Lithium Hexamethyldisilazide → HCID 86614577, compound

HRID 1723819Notes

Reaction equation

[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]([F:23])([F:22])[CH:19]([F:21])[F:20])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)(=[O:4])=[O:3].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C[O:35][C:36]([CH:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1)=O>C1COCC1>[F:22][C:18]([F:23])([O:17][C:14]1[CH:13]=[CH:12][C:11]([N:8]2[CH2:9][CH2:10][N:5]([S:2]([CH2:1][C:36]([CH:38]3[CH2:43][CH2:42][O:41][CH2:40][CH2:39]3)=[O:35])(=[O:3])=[O:4])[CH2:6][CH2:7]2)=[CH:16][CH:15]=1)[CH:19]([F:21])[F:20]

Participants

Conditions

Temperature: -10 °C

Procedure

The 1-(methylsulfonyl)-4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]piperazine (2.85 g, 0.008 mol) was dissolved in anhydrous THF (200 ml) and cooled to −10° C. under an argon atmosphere. 1.0M solution of lithium bis(trimethylsilyl)amide in THF (17.6 ml, 0.0176 mol) was added with cooling to −30° C. and the mixture added a solution of methyl-tetrahydro-2H-pyran-4-carboxylate (CAS Number 110238-91-0) in THF (2 ml). This was allowed to reach room temperature and stirred for 2 hours. The reaction was quenched with saturated NH4Cl solution and diluted with H2O and ethyl acetate. The organic phase was collected, dried over MgSO4, filtered and evaporated to dryness to yield crude 2-({4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]piperazin-1-yl}sulfonyl)-1-(tetrahydro-2H-pyran-4-yl)ethanone. (3.64 g, 97%)

Workup

temperaturewith cooling to −30° C.
customto reach room temperature
customThe reaction was quenched with saturated NH4Cl solution
additiondiluted with H2O and ethyl acetate
customThe organic phase was collected
dry with materialdried over MgSO4
filtrationfiltered
customevaporated to dryness

Sources & evidence

ORD record: ord-f26838ec33f34678a56adc62b279bdd4
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07485644B2

Reaction notes

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