Dimethylformamide dimethyl acetal → N-Benzyloxycarbonyl-3(R,S)-methoxycarbonyl-1,2,3,4-tetrahydroquinoline

HRID 863215Notes

Reaction equation

HRID 863215 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.[CH3:24]OC(OC)N(C)C>C1(C)C=CC=CC=1>[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][CH3:24])=[O:22])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 196975891-[(Benzyloxy)carbonyl]-1,2,3,4-tetrahydroquinoline-3-carboxylic acid

Product 1

HCID 19697580N-Benzyloxycarbonyl-3(R,S)-methoxycarbonyl-1,2,3,4-tetrahydroquinoline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.87 g of N-benzyloxycarbonyl-1,2,3,4-tetrahydroquinoline-3(R,S)-carboxylic acid and 5 ml of N,N-dimethylformamide dimethyl acetal are heated at 80° C. in 20 ml of toluene for 4 h. The reaction mixture is concentrated and the residue is purified by means of FC (50 g of silica gel, mobile phase D): Rf (D)=0.29; MS: (M)+ =325.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customthe residue is purified by means of FC (50 g of silica gel, mobile phase D)

Sources & evidence

ORD record
ord-2b4870854d734d74a223ff95b621fcde
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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