Allyl chloroformate → 3(R,S)-Allyloxycarbonylamino-1,2,3,4-tetrahydroquinoline

HRID 863311Notes

Reaction equation

[NH2:1][CH:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH2:3]1.[CH2:12]([O:15][C:16](Cl)=[O:17])[CH:13]=[CH2:14].C(NC(=O)[C@H](C)C[C@H](O)[C@@H](NC(OC(C)(C)C)=O)CC(C)(C)CC(N1C2C(=CC=CC=2)CC(NC(C2CC2)=O)C1)=O)CCC>>[CH2:12]([O:15][C:16]([NH:1][CH:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH2:3]1)=[O:17])[CH:13]=[CH2:14]

Participants

Reactant 3

HCID 18052Allyl chloroformate

HCID 40551181,2,3,4-Tetrahydroquinolin-3-amine

HCID 1317205275(S)-tert-butoxycarbonylamino-4(S)-hydroxy-2(R),7,7-trimethyl-8-[3(R,S)-cyclopropylcarbonylamino-1,2,3,4-tetrahydroquinolin-1-ylcarbonyl]-octanoic acid (N-butyl)amide

Product 1

HCID 196975483(R,S)-Allyloxycarbonylamino-1,2,3,4-tetrahydroquinoline

Procedure

In a manner analogous to that described in Example 109b) from 1.0 g of 1.0 g of 3(R,S)-amino-1,2,3,4-tetrahydroquinoline and 0.75 ml of allylchloroformate: Rf (P)=0.81; MS: M+ =232.

Sources & evidence

ORD record: ord-86f8d821755b4e6b9fbe16052b787399
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05719141

Reaction notes

Loading…