22494-02-6 → HCID 53713153, compound

HRID 1939476Notes

Reaction equation

C(OC([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11](O)([CH2:18][CH2:19][CH3:20])[CH2:10][CH2:9]1)=O)(C)(C)C.C(C1C2C(=CC=CC=2)NCC1)C>>[CH2:18]([CH:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[NH:8][CH2:9][CH2:10]1)[CH2:19][CH3:20]

Participants

Reactant 2

HCID 1086663722494-02-6

HCID 23433482HCID 23433482, compound

Product 1

HCID 53713153HCID 53713153, compoundYield 69.1%

Procedure

This compound was prepared from 1-tert-butyloxycarbonyl-1,2,3,4,-tetrahydro-4-hydroxy-4-propylquinoline (550 mg, 1.89 mmol) in the manner previously described for 4-ethyl-1,2,3,4-tetrahydroquinoline (EXAMPLE 345), affording 229 mg (66%) of the desired tetrahydroquinoline as a yellow oil (Rf 0.10, hexanes/EtOAc, 2:1). Data for (R/S)-1,2,3,4,-tetrahydro-4-propylquinoline: 1H NMR (400 MHz, CDCl3) 7.07 (d, 1H, J=7.6, 5-H), 7.02 (ddd, 1H, J=7.9, 7.9, 1.1, 7-H), 6.77 (dd, 1H, J=7.5, 7.4, 6-H), 6.67 (d, 1H, J=7.9, 8-H), 6.25 (br s, 1H, NH), 3.37 (ddd, 1H, J=11.5, 11.5, 3.5, 2-H), 3.30 (m, 1H, 2-H), 2.78 (dddd, 1H, J=10.0, 5.0, 5.0, 5.0, 4-H), 1.99 and 1.84 (2×m, 2×1H, 3-H), 1.68 (m, 1H, CH2CH2 CH3), 1.47 (m, 3H, CH2CH2CH3), 0.95 (t, 3H, J=7.3, CH3).

Sources & evidence

ORD record: ord-22a3634886994680b9fe06cab8287aac
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05696127

Reaction notes

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