(+-)-3-Quinuclidinol → HCID 123813074, compound

HRID 2274858Notes

Reaction equation

HRID 2274858 reaction equation
[N:1]([C@@H:4]1[CH2:6][C@H:5]1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[C:2]=[O:3].[N:13]12[CH2:20][CH2:19][CH:16]([CH2:17][CH2:18]1)[CH:15]([OH:21])[CH2:14]2>>[C:7]1([C@@H:5]2[CH2:6][C@H:4]2[NH:1][C:2](=[O:3])[O:21][CH:15]2[CH:16]3[CH2:19][CH2:20][N:13]([CH2:18][CH2:17]3)[CH2:14]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

3

Reactant 2

HCID 15381(+-)-3-QuinuclidinolHCID 255285trans-2-Phenylcyclopropyl isocyanate

Product 1

HCID 123813074HCID 123813074, compoundYield 28%

Procedure

Using general procedure A, (+/−)((1S,2R)-2-isocyanatocyclopropyl)benzene (117 uL, 0.780 mmol) and quinuclidin-3-ol gave (+/−) quinuclidin-3-yl(1R,2S)-2-phenylcyclopropylcarbamate (63 mg, 28%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.30-7.05 (m, 5H), 5.43 (br s, 1H), 4.77 (br s, 1H), 3.23 (dd, J=9.0, 14.0 Hz, 1H), 2.97-2.65 (m, 6H), 2.15-1.12 (m, 8H) ppm. 13C NMR (100 MHz, CDCl3) δ 157.1, 140.7, 140.2, 128.5, 126.8, 126.3, 71.5, 55.7, 47.5, 46.6, 32.7, 25.6, 25.2, 24.5, 19.5, 16.2 ppm. Purity: >99.9% UPLCMS (210 nm); retention time 0.67 min; (M+1) 287.

Sources & evidence

ORD record
ord-d0e3d8ed52b74513910e0208737887e3
Source dataset
uspto-grants-2015_09
Patent number
US09126993B2

Reaction notes

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