Tributylstannane → HCID 54008832, compound

HRID 975682Notes

Reaction equation

[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH2:9][C@H:8]1[CH:20]([C:22]1[CH:23]=[N:24][CH:25]=[N:26][CH:27]=1)Cl)=[O:6])[CH:2]=[CH2:3].C([SnH](CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][Si:13]([C:16]([CH3:18])([CH3:19])[CH3:17])([CH3:14])[CH3:15])[CH2:9][C@H:8]1[CH2:20][C:22]1[CH:23]=[N:24][CH:25]=[N:26][CH:27]=1)=[O:6])[CH:2]=[CH2:3]

Participants

Conditions

Temperature: 80 °C

Procedure

Under nitrogen atmosphere to a solution of 1-{(2S,4R)-1-allyloxycarbonyl-4-(t-butyldimethylsilyloxy)-pyrrolidin-2-yl }-1-(pyrimidin-5-yl)-1-chloromethane (37.4 g) in toluene (750 ml) were added firstly tributyltin hydride (29.1 g) and secondly azoisobutyronitrile (0.45 g) at room temperature. After the reaction mixture was stirred at 80° C. for two hours, it was cooled and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (400 g) (solvent; hexane:ethyl acetate=4:1 to 2:1 to 1:2) to give (2R,4R)-1-allyloxycarbonyl-4-t-butyldimethylsilyloxy-2-(pyrimidin-5-ylmethyl) pyrrolidine (29.1 g) as an oil.

Workup

temperatureit was cooled
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-fa587bfe36ae486bacc59f1f901df0b1
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05608056

Reaction notes

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