Methanol → tert-Butyl ethyl(2-(7-nitro-2H-benzo[b][1,4]oxazin-4(3H)-yl)ethyl)carbamate

HRID 424479ノート

反応式

HRID 424479 の反応式
[CH2:1]([N:3]([CH2:11][C:12]([N:14]1[CH2:19][CH2:18][O:17][C:16]2[CH:20]=[C:21]([N+:24]([O-:26])=[O:25])[CH:22]=[CH:23][C:15]1=2)=O)[C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7])[CH3:2].B.C1COCC1.CO>C1COCC1>[CH2:1]([N:3]([CH2:11][CH2:12][N:14]1[CH2:19][CH2:18][O:17][C:16]2[CH:20]=[C:21]([N+:24]([O-:26])=[O:25])[CH:22]=[CH:23][C:15]1=2)[C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:7])[CH3:8])[CH3:2]

参加物

5

反応物 3

HCID 887MethanolHCID 2723981Borane;tetrahydrofuranHCID 59144071tert-butyl ethyl(2-(7-nitro-2H-benzo[b][1,4]oxazin-4(3H)-yl)-2-oxoethyl)carbamate

生成物 1

HCID 59144101tert-Butyl ethyl(2-(7-nitro-2H-benzo[b][1,4]oxazin-4(3H)-yl)ethyl)carbamate収率 91%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A yellow solution of tert-butyl ethyl(2-(7-nitro-2H-benzo[b][1,4]oxazin-4(3H)-yl)-2-oxoethyl)carbamate (8.7 g, 23.8 mmol) in anhydrous THF (50 mL) under positive argon pressure was treated with borane-THF complex (1M in THF, 47.6 mL, 47.6 mmol) to give an orange solution. The mixture was refluxed for 20 minutes. It was then cooled in an ice bath and treated dropwise with MeOH (100 mL). The solution stirred for half an hour at room temperature, and the reaction was then concentrated. The residue was subjected to flash chromatography on silica gel using 1:9 EtOAc:hexanes to give an orange solid (7.5 g, 91%). 1H-NMR (DMSO-d6) δ 7.72 (dd, J=2.7, 9.0 Hz, 1H), 7.49-7.47 (m, 1H), 6.85-6.83 (m, 1H), 4.18 (t, J=4.2 Hz, 2H), 3.59-3.53 (m, 2H), 3.37-3.36 (m, 2H), 3.20-3.18 (m, 2H), 1.47 (s, 2H), 1.30 (br s, 9H), 1.02 (t, J=6.9 Hz, 3H); ESI-MS (m/z, %): 374 (MNa+, 86), 352 (MH+, 7.8), 296 (100), 252 (87).

後処理

  1. customto give an orange solution
  2. temperatureThe mixture was refluxed for 20 minutes
  3. temperatureIt was then cooled in an ice bath
  4. concentrationthe reaction was then concentrated

出典と根拠

ORDレコード
ord-e0b6efdf35ae4690a91fc7bcf3cd1197
出典データセット
uspto-grants-2012_01
特許番号
US08106043B2

反応ノート

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