Methyl iodide → HCID 178486000, compound

HRID 25562Notes

Reaction equation

[H-].[Na+].[CH2:3]([O:10][C:11](=[O:27])[NH:12][C@H:13]1[CH2:18][CH2:17][C@H:16]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH2:15][CH2:14]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.I[CH3:29].[NH4+].[Cl-]>CN(C=O)C>[CH2:3]([O:10][C:11](=[O:27])[N:12]([C@H:13]1[CH2:18][CH2:17][C@H:16]([O:19][Si:20]([C:23]([CH3:24])([CH3:26])[CH3:25])([CH3:21])[CH3:22])[CH2:15][CH2:14]1)[CH3:29])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a suspension of 0.58 g (55% in mineral oil, 13 mmol, 1.2 eq) sodium hydride in 20 ml DMF, a solution of 4.2 g (11 mmol) trans-[4-(tert-Butyl-dimethyl-silanyloxy)-cyclohexyl]-carbamic acid benzyl ester in 10 ml DMF was added slowly. The temperature was raised slowly to 50° C. and kept at that temperature for 1 h. At RT 0.9 ml (14 mmol; 1.3 eq) iodomethane were added and the mixture stirred over night. Additional 0.58 g (55% in mineral oil, 13 mmol, 1.2 eq) sodium hydride and 0.9 ml (14 mmol; 1.3 eq) iodomethane were added and the reaction mixture was stirred for 1 day. Aqueous NH4Cl solution was added and the inorganic phase was extracted with ether, washed with brine, dried over Na2SO4 and evaporated yielding 3.1 g (72%) trans-[4-(tert-Butyl-dimethyl-silanyloxy)-cyclohexyl]-methyl-carbamic acid benzyl ester.

Workup

stirringthe reaction mixture was stirred for 1 day
extractionthe inorganic phase was extracted with ether
washwashed with brine
dry with materialdried over Na2SO4
customevaporated

Sources & evidence

ORD record: ord-ba1933b5c4704898a39c00f2b5cc4dfe
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06858651B2

Reaction notes

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