HCID 68997730, compound → HCID 68999277, compound

HRID 1909644Notes

Reaction equation

COC(=O)CCCN1CCC[C@H]1COC1C=CC(CC2C=CC=CC=2)=CC=1.[CH2:28]([C:35]1[CH:56]=[CH:55][C:38]([O:39][CH2:40][C@H:41]2[CH2:45][CH2:44][CH2:43][N:42]2[CH2:46][CH2:47][CH2:48][C:49]2[O:53][NH:52][N:51]([CH3:54])[CH:50]=2)=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>>[CH2:28]([C:35]1[CH:56]=[CH:55][C:38]([O:39][CH2:40][C@@H:41]2[CH2:45][CH2:44][CH2:43][N:42]2[CH2:46][CH2:47][CH2:48][C:49]2[O:53][NH:52][N:51]([CH3:54])[CH:50]=2)=[CH:37][CH:36]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

Reactant 2

HCID 68997730HCID 68997730, compound

HCID 69001764HCID 69001764, compound

Product 1

HCID 68999277HCID 68999277, compoundYield 40%

Procedure

The title compound (0.210 mg, 40%) was prepared from 4-[(S)-2-(4-benzyl-penoxymethyl)-pyrrolidin-1-yl]-butyric acid methyl ester (337 mg, 1 mmol) by a similar procedure as that described for the synthesis of 5-{3-[(R)-2-(4-benzyl-phenoxymethyl)-pyrrolidin-1-yl]-propyl}-3-methyl-[1,2,3]oxadiazole: MS; m/z 392 (M+1); 1H NMR (400 HMz, CDCl3) δ 1.62-1.79 (m, 3H), 1.92-2.03 (m, 3H), 2.23 (m, 1H), 2.33 (s, 3H), 2.49 (m, 1H), 2.81-2.99 (m, 4H), 3.14 (m, 1H), 3.73 (dd, J1=6.4 Hz, J2=9.2 Hz, 1H), 3.86 (dd, J1=4.8 Hz, J2=9.6 Hz, 1H), 3.92 (s, 2H), 6.81 (dd, J1=2.0 Hz, J2=6.8 Hz, 2H), 7.08 (d, J=8.0 Hz, 2H), 7.16-7.29 (m, 5H).

Sources & evidence

ORD record: ord-7f3aa4b335dd46e7b954591c61ec0b2d
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598359B2

Reaction notes

Loading…