Ammonia → HCID 67286081, compound

HRID 2191381Notes

Reaction equation

[CH3:1][C:2]1([CH3:13])[O:6][C@@H:5]2[CH:7]=[CH:8][C@@H:9]([C@H:10]3[CH2:12][O:11]3)[C@@H:4]2[O:3]1.[NH3:14]>CO>[NH2:14][CH2:12][C@H:10]([C@H:9]1[C@H:4]2[C@H:5]([O:6][C:2]([CH3:13])([CH3:1])[O:3]2)[CH:7]=[CH:8]1)[OH:11]

Participants

Conditions

Temperature: 100 °C

Procedure

(3aS,4S,6aR)-2,2-dimethyl-4-((S)-oxiran-2-yl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxole (2-4) (3 g, 16.5 mmol, 1.0 equiv) was dissolved in a solution of ammonia in methanol (200 mL, 7 N). The mixture was heated in the microwave at 100° C. for 30 minutes. The reaction was concentrated to afford desired (S)-2-amino-1-((3aS,4S,6aR)-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)ethanol (2-5) as an amber oil that was carried to the next step without further purification. 1NMR (500 MHz, CDCl3): δ 5.98-5.86 (m, 1H); 5.91-5.65 (m, 1H); 5.13 (s, 1H); 4.80-4.45 (m, 1H); 3.03 (s, 1H); 2.95-2.83 (m, 2H); 2.74 (s, 2H); 2.61 (s, 2H); 1.41 (s, 3H); 1.35 (s, 3H).

Workup

concentrationThe reaction was concentrated

Sources & evidence

ORD record: ord-d5243a6c46a8482b81cb4bf24f84a02a
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329697B2

Reaction notes

Loading…