N,N,N-trimethyl-1,1-bis(1-methylethoxy)amine → N-Benzyloxycarbonyl-3(R,S)-isopropoxycarbonyl-1,2,3,4-tetrahydroquinoline

HRID 863230Notes

Reaction equation

HRID 863230 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.[CH:24](OC(OC(C)C)N(C)C)([CH3:26])[CH3:25].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(C(OCC)=O)C1)=O)CCC>>[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][CH:24]([CH3:26])[CH3:25])=[O:22])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 87682N,N,N-trimethyl-1,1-bis(1-methylethoxy)amineHCID 196975891-[(Benzyloxy)carbonyl]-1,2,3,4-tetrahydroquinoline-3-carboxylic acidHCID 1317205115(S)-tert-butoxycarbonylamino-4(S)-hydroxy-2(R),7,7-trimethyl-8-[3(R,S)-ethoxycarbonyl-1,2,3,4-tetrahydroquinolin-1-ylcarbonyl]-octanoic acid (N-butyl)amide

Product 1

HCID 19697655N-Benzyloxycarbonyl-3(R,S)-isopropoxycarbonyl-1,2,3,4-tetrahydroquinoline

Procedure

The title compound is prepared analogously to Example 1s) starting from 1.87 g of N-benzyloxycarbonyl-1,2,3,4-tetrahydroquinoline-3(R,S)-carboxylic acid and 5.1 ml of N,N-dimethylformamide diisopropyl acetal Rf (A)=0.78; MS: (M)+ =353.

Sources & evidence

ORD record
ord-aeb6b980b9d34ae49539c4e6195f936e
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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