Dichloromethane → Tert-butyl (2S,3R)-3-(tert-butyldimethylsilyloxy)-4-((S)-2,2-dimethyl-6-neopentyl-1,2,3,4-tetrahydroquinolin-4-ylamino)-1-(3-fluorophenyl)butan-2-ylcarbamate

HRID 20039

반응식

HRID 20039 반응식
[Si:1]([O:8][C@H:9]([CH:27]=O)[C@@H:10]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:29][C:30]1([CH3:46])[CH2:39][C@H:38]([NH2:40])[C:37]2[C:32](=[CH:33][CH:34]=[C:35]([CH2:41][C:42]([CH3:45])([CH3:44])[CH3:43])[CH:36]=2)[NH:31]1.C(Cl)Cl.COC(OC)OC.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[Si:1]([O:8][C@H:9]([CH2:27][NH:40][C@@H:38]1[C:37]2[C:32](=[CH:33][CH:34]=[C:35]([CH2:41][C:42]([CH3:45])([CH3:44])[CH3:43])[CH:36]=2)[NH:31][C:30]([CH3:46])([CH3:29])[CH2:39]1)[C@@H:10]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:25])[CH3:24])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

참가 물질

6

반응물 5

HCID 6344DichloromethaneHCID 9005Trimethyl orthoformateHCID 5049666Sodium triacetoxyborohydrideHCID 67305468(S)-2,2-dimethyl-6-neopentyl-1,2,3,4-tetrahydroquinolin-4-amineHCID 86614118tert-butyl (2S,3S)-3-(tert-butyldimethylsilyloxy)-1-(3-fluorophenyl)-4-oxobutan-2-ylcarbamate

생성물 1

HCID 86614130Tert-butyl (2S,3R)-3-(tert-butyldimethylsilyloxy)-4-((S)-2,2-dimethyl-6-neopentyl-1,2,3,4-tetrahydroquinolin-4-ylamino)-1-(3-fluorophenyl)butan-2-ylcarbamate

실험 절차

To a solution of tert-butyl (2S,3S)-3-(tert-butyldimethylsilyloxy)-1-(3-fluorophenyl)-4-oxobutan-2-ylcarbamate (0.148 g, 0.360 mmol) and (S)-2,2-dimethyl-6-neopentyl-1,2,3,4-tetrahydroquinolin-4-amine (0.0886 g, 0.360 mmol) in DCM (7.19 ml, 0.360 mmol) was added trimethoxymethane (0.394 ml, 3.60 mmol). The resulting solution was stirred for 1 hour at which time, sodium triacetoxyborohydride (0.229 g, 1.08 mmol) was added. The solution was then stirred for 30 minutes, quenched with saturated Rochelle's salt and stirred for an additional 20 minutes. The mixture was transferred to a sep. funnel containing DCM and H2O. The aqueous layer was washed 4× with DCM. The organic layers were combined, washed 1× with brine, dried with MgSO4, filtered and concentrated to afford the title compound. MS m/z: 642 (M+1).

후처리

  1. additionwas added
  2. customquenched with saturated Rochelle's salt
  3. stirringstirred for an additional 20 minutes
  4. additionfunnel containing DCM and H2O
  5. washThe aqueous layer was washed 4× with DCM
  6. washwashed 1× with brine
  7. dry with materialdried with MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-0feb4bd794af4aba8348f04397537e43
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745484B2

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