Methyl iodide → HCID 19041724, compound

HRID 1683983Notes

Reaction equation

[Li][CH2:2]CCC.CC1(C)CCCC(C)(C)N1.[Br:16][C:17]1[CH:43]=[CH:42][C:20]([CH2:21][N:22]2[C:30]3[C:25](=[CH:26][C:27]([O:31][CH3:32])=[CH:28][CH:29]=3)[C:24]([CH2:33][CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[C:23]2[CH3:41])=[CH:19][CH:18]=1.CN(P(N(C)C)(N(C)C)=O)C.CI>C1COCC1>[Br:16][C:17]1[CH:43]=[CH:42][C:20]([CH2:21][N:22]2[C:30]3[C:25](=[CH:26][C:27]([O:31][CH3:32])=[CH:28][CH:29]=3)[C:24]([CH2:33][CH2:34][CH:35]([CH3:2])[C:36]([O:38][CH2:39][CH3:40])=[O:37])=[C:23]2[CH3:41])=[CH:19][CH:18]=1

Participants

Conditions

Temperature: -78 °C

Procedure

n-BuLi (1.6M in hexane, 6.4 mL, 10.3 mmol) was added slowly to 2,2,6,6-tetramethylpiperidine at -10° C. and the slurry was stirred 30 min, then cooled to -78° C. and diluted with 25 mL degassed THF. This solution was transferred via cannula into a 50 mL (degassed) THF solution of ester from Step 1 (4.15 g, 9.3 mmol) at -78° C. After stirring 1-- h, HMPA (1.6 mL, 9.3 mmol) was added and 30 min later CH3I (5.8 mL, 93 mmol) was added. The reaction mixture was stirred 12 h at -78° C., then quenched with saturated NH4Cl and extracted with Et2O and ethyl acetate. The organic phase was washed with aqueous Na2S2O5, water, brine and dried over MgSO4. Purification by flash chromatography (15% ethyl acetate in hexane) provided 2.5 g of the title compound.

Workup

additiondiluted with 25 mL
customdegassed THF
additionwas added
stirringThe reaction mixture was stirred 12 h at -78° C.
customquenched with saturated NH4Cl
extractionextracted with Et2O and ethyl acetate
washThe organic phase was washed with aqueous Na2S2O5, water, brine
dry with materialdried over MgSO4
customPurification by flash chromatography (15% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-00176d8d369c4a7bb6dfbfb299643108
Source dataset: uspto-grants-1997_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05639780

Reaction notes

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