Acetic Acid → Ethyl (3S, 4aR, 6S, 8aR) 6-amino-2-methoxycarbonyl-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinol-3-carboxylate

HRID 583836ノート

反応式

HRID 583836 の反応式
O=[C:2]1[CH2:11][CH2:10][CH:9]2[CH:4]([CH2:5][CH:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:7]([C:12]([O:14][CH3:15])=[O:13])[CH2:8]2)[CH2:3]1.C([NH2:28])C1C=CC=CC=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[NH2:28][C@H:2]1[CH2:11][CH2:10][C@@H:9]2[C@@H:4]([CH2:5][C@@H:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:7]([C:12]([O:14][CH3:15])=[O:13])[CH2:8]2)[CH2:3]1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 7504BenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 148779783-Ethyl 2-Methyl 6-oxooctahydroisoquinoline-2,3(1H)-dicarboxylate

生成物 1

HCID 60023865Ethyl (3S, 4aR, 6S, 8aR) 6-amino-2-methoxycarbonyl-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinol-3-carboxylate収率 174.6%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

To a room temperature solution of ethyl 6-oxo-2-methoxycarbonyl-decahydroisoquinoline-3-carboxylate (4 g, 14.1 mmol), benzylamine (1.71 g, 15.9 mmol), and acetic acid (1.27 g, 21.2 mmol) in 1,2-dichloroethane (20 ml), sodium triacetoxyborohydride (5 g, 23.3 mmol) was added. The mixture was stirred under an atmosphere of nitrogen for 15 hours at room temperature. The reaction was quenched by adding aqueous saturated sodium bicarbonate, and extracted with dichloromethane three times. The organic layer was dried over sodium sulfate and evaporated to give 7 g of the title compound. The crude material was used in next step without further purification.

後処理

  1. customThe reaction was quenched
  2. additionby adding aqueous saturated sodium bicarbonate
  3. extractionextracted with dichloromethane three times
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customevaporated

出典と根拠

ORDレコード
ord-61b9cc8beaa34d6a80fe2957f208dc63
出典データセット
uspto-grants-2005_08
特許番号
US06924294B2

反応ノート

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