Water → tert-Butyl 4-(2-(4-nitronaphthalen-1-yloxy)ethyl)pyridin-2-ylcarbamate

HRID 872396ノート

反応式

HRID 872396 の反応式
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:5]=1.[H-].[Na+].F[C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]([N+:31]([O-:33])=[O:32])=[CH:23][CH:22]=1.O>C1COCC1.CCOC(C)=O>[N+:31]([C:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:21]([O:1][CH2:2][CH2:3][C:4]2[CH:9]=[CH:8][N:7]=[C:6]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:16])[CH3:15])[CH:5]=2)=[CH:22][CH:23]=1)([O-:33])=[O:32]

参加物

7

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2617641-Fluoro-4-nitronaphthaleneHCID 58416767tert-Butyl (4-(2-hydroxyethyl)pyridin-2-yl)carbamate

生成物 1

HCID 58416756tert-Butyl 4-(2-(4-nitronaphthalen-1-yloxy)ethyl)pyridin-2-ylcarbamate収率 106.6%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of tert-butyl 4-(2-hydroxyethyl)pyridin-2-ylcarbamate (11) (6.00 g, 25.2 mmol) in THF (70 mL) was added sodium hydride (2.52 g, 63.0 mmol, 60 wt %) at 0° C. The bright yellow suspension was stirred for 20 min at 0° C. before the addition of 1-fluoro-4-nitronaphthalene (4.81 g, 25.2 mmol) in a single portion. After stirring at RT for 2 hr, water (100 mL) was added followed by EtOAc (100 mL). The solid formed between the layers was collected by filtration and the organic phase was washed with saturated aq NaHCO3(100 mL), brine (100 mL) and dried. The volatiles were removed to give an orange solid. The solids were combined and triturated from MeOH (50 mL) to give tert-butyl 4-(2-(4-nitronaphthalen-1-yloxy)ethyl)pyridin-2-ylcarbamate (12) as a yellow solid (11.0 g, 98%): m/z 410 (M+H)+ (ES+).

後処理

  1. customThe solid formed between the layers
  2. filtrationwas collected by filtration
  3. washthe organic phase was washed with saturated aq NaHCO3(100 mL), brine (100 mL)
  4. customdried
  5. customThe volatiles were removed
  6. customto give an orange solid
  7. customtriturated from MeOH (50 mL)

出典と根拠

ORDレコード
ord-2a12c4ad17504f4b951db8335d0a242c
出典データセット
uspto-grants-2015_03
特許番号
US08975285B2

反応ノート

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