Vinyl Acetate → HCID 14589999, compound

HRID 1073668Notes

Reaction equation

[CH2:1]1[C@H:9]([OH:10])[C@H:8]2[N:3]([CH2:4][C@H:5]([OH:13])[C@@H:6]([OH:12])[C@@H:7]2[OH:11])[CH2:2]1.[C:14](OC=C)(=[O:16])[CH3:15]>>[C:14]([O:10][CH:9]1[CH:8]2[N:3]([CH2:4][CH:5]([OH:13])[CH:6]([OH:12])[CH:7]2[OH:11])[CH2:2][CH2:1]1)(=[O:16])[CH3:15]

Participants

Reactant 2

HCID 7904Vinyl Acetate

HCID 54445Castanospermine

Product 1

HCID 14589999HCID 14589999, compoundYield 91%

Procedure

The same general procedure was repeated using castanospermine and vinyl acetate (2.2 mmol) and a reaction time of 84 hours to give [1S-(1α, 6β,7α, 8β, 8aβ)]-octahydro-1,6,7,8-indolizinetetrol 1-acetate melting at about 151°-153° C. (yield, 91%)

Sources & evidence

ORD record: ord-2a83b1d53c1a4524a63096f14c0745a1
Source dataset: uspto-grants-1990_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04970317

Reaction notes

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