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 657136ノート

反応式

HRID 657136 の反応式
[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]

参加物

6

反応物 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

生成物 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)carbamate収率 78%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6212Chloroform溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-dbcc701df83a449d963589d47d0720c7
出典データセット
uspto-grants-2011_12
特許番号
US08071592B2

反応ノート

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