Water → HCID 500054, compound

HRID 2051157Notes

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](Cl)(=[O:18])[CH2:15][CH2:16][CH3:17].O.C(Cl)Cl>N1C=CC=CC=1.C(Cl)(Cl)Cl.CO>[C:14]([O:13][CH:5]1[CH:6]([OH:12])[CH:7]([OH:11])[CH:8]2[N:3]([CH2:2][CH2:1][CH:9]2[OH:10])[CH2:4]1)(=[O:18])[CH2:15][CH2:16][CH3:17]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred suspension of 1.5 g of castanospermine in 15 ml of pyridine cooled at 0° C. in an ice-bath was added dropwise 1.0 g of butyryl chloride. The mixture was stirred at room temperature for 3 days and added to a 1:1 mixture of water:methylene chloride (400 ml). After partitioning, the aqueous phase was concentrated in vacuo to provide an oily residue which was fractionated by radial thin layer chromatography (silica gel, 2 mm thickness plate, 2:8 methanol: chloroform) to provide 68 mg of [1S-(lα, 6β, 7α, 8β, 8αβ) ]-octahydro-1,6,7,8-indolizinetetrol 6-butanoate, homogeneous by thin layer chromatography (silica gel, 2:8 methanol: chloroform, Rf=0.5). Recrystallization of the product from 5:95 isopropanol:hexane gave a colorless solid melting at 113-114° C. NMR (CDCl3) δ 3.5-3.8 (2t, 2H, C7 --H, and C8 --H), 4.4 (m, 1H, C1 ---H), 4.95 (m, 1H, C6 --H). MS (CI--CH4) 260 (MH+), 242 (MH+ --H2O), 172 (MH+ --C3H7CO2H). Similarly, when the above procedure was repeated using acetyl chloride or propionyl chloride, the following monoesters were obtained:

Workup

customAfter partitioning
concentrationthe aqueous phase was concentrated in vacuo
customto provide an oily residue which

Sources & evidence

ORD record: ord-8352b5d151eb4148b6c3bdfadf313b79
Source dataset: uspto-grants-1991_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05017563

Reaction notes

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