Sodium triacetoxyborohydride → cis-1,1-Dimethylethyl ({(3rs,5rs)-5-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-[2-(7-fluoro-2-oxo-1 (2h)-quinolinyl)ethyl]-3-piperidinyl}methyl)carbamate

HRID 657136노트

반응식

HRID 657136 반응식
[CH3:1][C:2]([Si:5]([CH3:23])([CH3:22])[O:6][C@H:7]1[CH2:12][NH:11][CH2:10][C@@H:9]([CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:8]1)([CH3:4])[CH3:3].[F:24][C:25]1[CH:34]=[C:33]2[C:28]([CH:29]=[CH:30][C:31](=[O:38])[N:32]2[CH2:35][CH:36]=O)=[CH:27][CH:26]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CO.C(Cl)(Cl)Cl>[CH3:4][C:2]([Si:5]([CH3:23])([CH3:22])[O:6][C@H:7]1[CH2:12][N:11]([CH2:36][CH2:35][N:32]2[C:33]3[C:28](=[CH:27][CH:26]=[C:25]([F:24])[CH:34]=3)[CH:29]=[CH:30][C:31]2=[O:38])[CH2:10][C@@H:9]([CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:8]1)([CH3:1])[CH3:3]

참가 물질

6

반응물 3

HCID 5049666Sodium triacetoxyborohydrideHCID 86635311(7-Fluoro-2-oxo-1(2H)-quinolinyl)acetaldehydeHCID 131729313cis-1,1-Dimethylethyl [((3rs,5rs)-5-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-3-piperidinyl)methyl]carbamate

생성물 1

HCID 131729314cis-1,1-Dimethylethyl ({(3rs,5rs)-5-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-[2-(7-fluoro-2-oxo-1 (2h)-quinolinyl)ethyl]-3-piperidinyl}methyl)carbamate수율 78%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6212Chloroform용매

실험 절차

To cis-1,1-dimethylethyl [((3RS,5RS)-5-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-3-piperidinyl)methyl]carbamate (350 mg; 1.0 mmol) in MeOH (2 ml) and CHCl3 (8 ml) was added (7-fluoro-2-oxo-1(2H)-quinolinyl)acetaldehyde (for a preparation see Example 2(d) (200 mg; 1.0 mmol) and the reaction was allowed to stir at room temperature under N2 for 8 hours. Na(OAc)3BH (530 mg; 2.5 mmol) was added and the reaction was allowed to stir at room temperature under nitrogen for an additional 14 hours. The solvents were removed and the crude residue was purified by chromatography on silica gel using a 0-10% MeOH/DCM gradient to provide the desired compound (415 mg; 78%) as a colorless oil.

후처리

  1. stirringto stir at room temperature under nitrogen for an additional 14 hours
  2. customThe solvents were removed
  3. customthe crude residue was purified by chromatography on silica gel using a 0-10% MeOH/DCM gradient

출처 및 근거

ORD 기록
ord-dbcc701df83a449d963589d47d0720c7
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071592B2

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