Isobutyl iodide → HCID 69795369, compound

HRID 1743249Notes

Reaction equation

[CH2:1]([C@@H:4]1[C:9](=[O:10])[O:8][C@H:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C@H:6]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:5]1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:2]=[CH2:3].C1OCCOCCOCCOCCOC1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH2:55](I)[CH:56]([CH3:58])[CH3:57].[Cl-].[NH4+]>C1COCC1>[CH2:1]([C@:4]1([CH2:55][CH:56]([CH3:58])[CH3:57])[C:9](=[O:10])[O:8][C@H:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C@H:6]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:5]1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:2]=[CH2:3]

Participants

Conditions

Temperature: -78 °C

Procedure

1 g of tert-butyl (3R,5S,6R)-3-allyl-2-oxo-5,6-diphenylmorpholine-4-carboxylate was dissolved in 20 ml of THF. 3 ml of 15-crown-5 were added, and the mixture was cooled to −78° C. Then 1.4 ml of a 2 M solution of NaHMDS in THF were added dropwise. The mixture was stirred for 10 min and then 300 μl of isobutyl iodide were added dropwise. The temperature was allowed to rise to 0° C. over the course of 6 h, and then the reaction was stopped by adding 50 ml of saturated ammonium chloride solution. The aqueous phase was extracted 3 times with 50 ml of ethyl acetate each time, and the combined organic phases were dried with MgSO4. The solvents were removed in vacuo and the residue was chromatographed on silica gel with heptane/ethyl acetate 10:1.

Workup

customto rise to 0° C. over the course of 6 h
extractionThe aqueous phase was extracted 3 times with 50 ml of ethyl acetate each time
dry with materialthe combined organic phases were dried with MgSO4
customThe solvents were removed in vacuo
customthe residue was chromatographed on silica gel with heptane/ethyl acetate 10:1

Sources & evidence

ORD record: ord-3590330246b846f1bc74a138015384c8
Source dataset: uspto-grants-2006_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07008957B2

Reaction notes

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