Ammonia → HCID 67285542, compound

HRID 2191373Notes

Reaction equation

[CH3:1][C:2]1([CH3:34])[O:6][C@@H:5]2[C:7]([CH2:13][O:14][C:15]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:8][C@@H:9]([C@H:10]3[CH2:12][O:11]3)[C@@H:4]2[O:3]1.[NH3:35]>CO>[NH2:35][CH2:12][C@H:10]([C@H:9]1[C@H:4]2[C@H:5]([O:6][C:2]([CH3:34])([CH3:1])[O:3]2)[C:7]([CH2:13][O:14][C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:8]1)[OH:11]

Participants

Conditions

Temperature: 100 °C

Procedure

(3aS,4S,6aR)-2,2-dimethyl-4-((S)-oxiran-2-yl)-6-(trityloxymethyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxole (1-4) (2 g, 4.0 mmol, 1.0 equiv) was dissolved in a solution of ammonia in methanol (100 mL, 7 N). The mixture was heated in the microwave at 100° C. for 30 min. The reaction was concentrated to afford (S)-2-amino-1-((3aS,4S,6aR)-2,2-dimethyl-6-(trityloxymethyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)ethanol (1-5) as an amber solid that was carried to the next step without further purification. 1H NMR (500 MHz, CDCl3) δ 7.21-7.45 (m, 15H), 5.81 (2 s, 1H), 5.00 (t, 1H, J=5 Hz), 4.57-4.70 (2 d, 1H, J=5.5 Hz), 3.77 (d, 1H, J=14 Hz), 3.66 (d, 1H, J=14 Hz), 3.31 (m, 1H), 2.57-2.88 (m, 2H), 1.30 (s, 3H), 1.29 (s, 3H). LRMS m/z (M+H) 472.1 found, 472.2 required.

Workup

concentrationThe reaction was concentrated

Sources & evidence

ORD record: ord-c057937eff39473abc4db33f7ea64d4e
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329697B2

Reaction notes

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