Triethylamine → (4aR,8aR)-6-benzyl 1-tert-butyl hexahydro-1H-pyrido[3,4-b][1,4]oxazine-1,6(7H)-dicarboxylate

HRID 1852726ノート

反応式

HRID 1852726 の反応式
[N:1]1([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6][CH2:5][O:4][C@@H:3]2[CH2:7][NH:8][CH2:9][CH2:10][C@@H:2]12.Cl[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20].C(N(CC)CC)C>C(Cl)Cl>[N:1]1([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6][CH2:5][O:4][C@@H:3]2[CH2:7][N:8]([C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])[CH2:9][CH2:10][C@@H:2]12

参加物

5

反応物 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 86724487tert-butyl (4aR,8aR)-octahydro-1H-pyrido[3,4-b][1,4]oxazine-1-carboxylate

生成物 1

HCID 86724486(4aR,8aR)-6-benzyl 1-tert-butyl hexahydro-1H-pyrido[3,4-b][1,4]oxazine-1,6(7H)-dicarboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To tert-butyl (4aR,8aR)-octahydro-1H-pyrido[3,4-b][1,4]oxazine-1-carboxylate (250 mg, 1.03 mmol) dissolved in DCM (2 mL) was added benzyl chloroformate (0.21 mL, 1.44 mmol). Triethylamine (0.4 mL, 2.89 mmol) was added slowly and stirred for 3 hours at room temperature. The reaction was quenched with saturated aqueous sodium bicarbonate. The aqueous layer was extracted with DCM, and the combined organic layers were dried over sodium sulfate, filtered, and concentrated to afford (4aR,8aR)-6-benzyl 1-tert-butyl hexahydro-1H-pyrido[3,4-b][1,4]oxazine-1,6(7H)-dicarboxylate. 1H NMR (500 MHz, CDCl3) δ 7.40-7.30 (m, 5H), 5.12 (s, 2H), 4.40-4.15 (m, 1H), 3.93-3.87 (m, 1H), 3.86-3.79 (m, 1H), 3.77-3.71 (m, 1H), 3.42-3.29 (m, 2H), 3.19-3.13 (m, 1H), 2.81-2.48 (m, 2H), 1.76-1.66 (m, 1H), 1.58 (s, 2H), 1.45 (s, 9H).

後処理

  1. customThe reaction was quenched with saturated aqueous sodium bicarbonate
  2. extractionThe aqueous layer was extracted with DCM
  3. dry with materialthe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-d4a3eaee8da546c7871d5b15b980d7dc
出典データセット
uspto-grants-2015_02
特許番号
US08962611B2

反応ノート

読み込み中…