Water → (R)-Quinuclidin-3-yl(3-(8-(1,3-dioxolan-2-yl)octyloxy)-phenyl)(phenyl)-methylcarbamate

HRID 332650Notes

Reaction equation

[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH:21](C2C=CC=CC=2)[NH2:22])[CH:18]=[CH:19][CH:20]=1.[C:29](Cl)(=[O:39])[O:30][C@@H:31]1[CH:36]2[CH2:37][CH2:38][N:33]([CH2:34][CH2:35]2)[CH2:32]1.O>N1C=CC=CC=1>[N:33]12[CH2:38][CH2:37][CH:36]([CH2:35][CH2:34]1)[C@@H:31]([O:30][C:29](=[O:39])[N:22]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH2:21][C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([O:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH:2]3[O:1][CH2:5][CH2:4][O:3]3)[CH:16]=1)[CH2:32]2

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of (3-(8-(1,3-dioxolan-2-yl)octyloxy)phenyl)-(phenyl)-methanamine (0.62 g, 1.62 mmol) in pyridine (10 mL) at 0° C., (R)-quinuclidin-3-yl carbonochloridate (0.48 g, 2.1 mmol) was added. The reaction was stirred at 0° C. for 1 hour and then allowed to warm to RT for 16 hours. Water was added to the reaction mixture and extracted with ethyl acetate (×3). The combined extracts were washed with brine, dried (sodium sulfate), filtered, and concentrated under reduced pressure. The crude material was purified by chromatography on a KP-NH Biotage cartridge eluting with 0-20% methanol in ethyl acetate to afford the title compound (0.67 g, 78%).

Workup

temperatureto warm to RT for 16 hours
extractionextracted with ethyl acetate (×3)
washThe combined extracts were washed with brine
dry with materialdried (sodium sulfate)
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude material was purified by chromatography on a KP-NH Biotage cartridge
washeluting with 0-20% methanol in ethyl acetate

Sources & evidence

ORD record: ord-70b4a27b31ca439fbb25617d0cf3c9bd
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877774B2

Reaction notes

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