Cyclopentanol → HCID 19381025, compound

HRID 258297Notes

Reaction equation

[CH:1]1[C:14]2[C:13]3([CH2:16][N:17]4[CH2:22][CH2:21][CH:20]([NH:23][C:24](=[O:27])[CH2:25]Br)[CH2:19][CH2:18]4)[CH2:15][CH:6]([C:7]4[C:12]3=[CH:11][CH:10]=[CH:9][CH:8]=4)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH:28]1([OH:33])[CH2:32][CH2:31][CH2:30][CH2:29]1>>[CH:1]1[C:14]2[C:13]3([CH2:16][N:17]4[CH2:22][CH2:21][CH:20]([NH:23][C:24](=[O:27])[CH2:25][O:33][CH:28]5[CH2:32][CH2:31][CH2:30][CH2:29]5)[CH2:19][CH2:18]4)[CH2:15][CH:6]([C:7]4[C:12]3=[CH:11][CH:10]=[CH:9][CH:8]=4)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

Reactant 2

HCID 7298Cyclopentanol

HCID 19381078HCID 19381078, compound

Product 1

HCID 19381025HCID 19381025, compound

Procedure

Using a procedure similar to that described in Example 21 except starting with N-(1-[9,10-dihydro-9,10-methanoanthracen-9-ylmethyl]-4-piperidyl)-2-bromoacetamide (described in Example 38a) and cyclopentanol, the title compound was obtained as a white solid (63%), mp 127.0°-8.0° C.; MS(CI): 431 (M+H); NMR (300 MHz,DMSO-d6): 1.48(br m, 4H), 1.62(br m, 8H), 2.28(br m, 2H), 2.45(s, 2H), 2.94(br m, 2H), 3.34(s, submerged, 2H), 3.60(br m, 1H), 3.74(2, 2H), 3.89(sextet, 1H, J=3.9 Hz), 4.30(s, 1H), 6.91(br m, 4H), 7.18(d, 2H, J=6.2 Hz), 7.26(d, 2H, J=6.2 Hz), 7.33(d, 1H, J=8.3 Hz).

Sources & evidence

ORD record: ord-75dc52478b9f4e83b49d9cc47217d0c6
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05266570

Reaction notes

Loading…