Dimethylformamide diethylacetal → N-Benzyloxycarbonyl-3(R,S)-ethoxycarbonyl-1,2,3,4-tetrahydroquinoline

HRID 863229Notes

Reaction equation

[CH2:1]([O:8][C:9]([N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH:13]([C:21]([OH:23])=[O:22])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:24](OC(OCC)N(C)C)[CH3:25]>>[CH2:1]([O:8][C:9]([N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH:13]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 70913Dimethylformamide diethylacetal

HCID 196975891-[(Benzyloxy)carbonyl]-1,2,3,4-tetrahydroquinoline-3-carboxylic acid

Product 1

HCID 19697614N-Benzyloxycarbonyl-3(R,S)-ethoxycarbonyl-1,2,3,4-tetrahydroquinoline

Procedure

The title compound is prepared analogously to Example 1s) starting from 1.5 g of N-benzyloxycarbonyl-1,2,3,4-tetrahydroquinoline-3(R,S)-carboxylic acid and 3.7 ml of N,N-dimethylformamide diethyl acetal and is purified by means of FC (100 g of silica gel, mobile phases D and B). This gives the title compound: Rf (A)=0.75; MS: (M)+ =339.

Workup

customThe title compound is prepared analogously to Example 1s)
customis purified by means of FC (100 g of silica gel, mobile phases D and B)

Sources & evidence

ORD record: ord-9837505786ec4eb1bb0b81b00ac6d1de
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05719141

Reaction notes

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