1-[(Benzyloxy)carbonyl]-1,2,3,4-tetrahydroquinoline-3-carboxylic acid → Benzyl 3-(hydroxymethyl)-1,2,3,4-tetrahydroquinoline-1-carboxylate

HRID 863317Notes

Reaction equation

HRID 863317 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](O)=[O:22])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCCC1.CO>[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]([CH2:21][OH:22])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

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

Product 1

HCID 19697547Benzyl 3-(hydroxymethyl)-1,2,3,4-tetrahydroquinoline-1-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

14.0 g of N-benzyloxycarbonyl-3(R,S)-carboxy-1,2,3,4-tetrahydroquinoline are stirred in 400 ml of tetrahydrofuran with 9.0 ml of 10M borane-dimethylsulfide complex at 25° C. for 16 h. The reaction mixture is diluted several times with methanol and evaporated. The crude product is recrystallized from ethyl acetate/hexane: mp 62°-4° C.; Rf (X)=0.50; FAB-MS: (M+H)+ =298; anal. calc. for C18H19NO3 : C 72.71%, H 6.44%, N 4.71%; found C 72.84%, H 6.35%, N 4.75%.

Workup

  1. customevaporated
  2. customThe crude product is recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-389000a709074707b3952252bf4e60da
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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