HCID 73110260, compound → (3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol

HRID 2404967Notes

Reaction equation

[CH3:1][C:2]1([CH3:12])[O:10][CH:9]2[CH:4]([CH:5]3[CH2:11][CH:8]2[O:7][NH:6]3)[O:3]1>[Pd].CO>[NH2:6][C@H:5]1[C@@H:4]2[O:3][C:2]([CH3:1])([CH3:12])[O:10][C@@H:9]2[C@@H:8]([OH:7])[CH2:11]1

Participants

Conditions

Temperature: 20 °C

Procedure

Under a pressurized hydrogen atmosphere (3 atm), a suspension of 4,4-dimethyl-3,5,8-trioxa-9-aza-tricyclo[5.2.1.02,6]decane (16.7 g, 97.55 mmol, 1.00 equiv.), 10% palladium on carbon (1.67 g), and methanol (250 mL) was stirred at about 20° C. for about 60 minutes. After filtering the solution, the resulting filtrate was concentrated in vacuo to give the title product as a white solid (16.8 g; yield=99%). MS: m/z=174 (MH)+.

Workup

filtrationAfter filtering the solution
concentrationthe resulting filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-4a59a90a89fb4f73be2c5358d53f18bd
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802850B2

Reaction notes

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