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

HRID 863317노트

반응식

HRID 863317 반응식
[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

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

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%.

후처리

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

출처 및 근거

ORD 기록
ord-389000a709074707b3952252bf4e60da
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05719141

반응 노트

불러오는 중…