(1S,2R)-(-)-1-Amino-2-indanol → (R)-2-Benzyl-2,4-dihydroxy-N-((1S,2R)-2-hydroxy-indan-1-yl)-butyramide

HRID 1158507Notes

Reaction equation

[CH2:1]([C:8]1([OH:14])[CH2:12][CH2:11][O:10][C:9]1=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OC1C=CC=CN=1.[CH2:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C@H:24]([NH2:31])[C@@H:23]1[OH:32]>ClCCl>[CH2:1]([C@@:8]([OH:14])([CH2:12][CH2:11][OH:10])[C:9]([NH:31][C@H:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:22][C@H:23]1[OH:32])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

3-Benzyl-3-hydroxy-dihydro-furan-2-one (21c) (0.5 g, 2.6 mmol) and 2-hyroxypyridine (0.27 g, 2.8 mmol) in dry dichloromethane (15 mL) was added (1S,2R)-(−)-cis-1-amino-2-indanol (0.43 g, 2.8 mmol). The reaction mixture was stirred at 50° C. for 24 h and then evaporated. The residue was dissolved in ethyl acetate (80 mL) and washed with 1M HCl (20 mL), followed by saturated aqueous NaHCO3 (20 mL), and thereafter dried, filtered, and concentrated. The residue purified by silica gel flash chromatography using petroleum ether:acetone (3:1) gave 0.26 g of first eluted (compound 21d-(S)) and 0.33 g of second eluted (compound 21d-(R)) together in 66% yield of the title compounds.

Workup

customevaporated
dissolutionThe residue was dissolved in ethyl acetate (80 mL)
washwashed with 1M HCl (20 mL)
customdried
filtrationfiltered
concentrationconcentrated
customThe residue purified by silica gel flash chromatography
customgave 0.26 g
washof first eluted (compound 21d-(S)) and 0.33 g

Sources & evidence

ORD record: ord-b3e8dcaf45f94753917b91c9f15ce44e
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07807677B2

Reaction notes

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