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Tetrahydrofuran → methyl 1-{1-[2-(7-methoxy-2,2-dimethyl-4-oxochroman-8-yl)ethyl]piperidin-4-yl}-1H-indole-6-carboxylate

HRID 1640062
ノート
印刷プレビュー

反応式

HRID 1640062 の反応式
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([O:19][CH3:20])=[O:18])[CH:15]=3)[CH:10]=[CH:9]2)[CH2:4][CH2:3]1.[CH3:21][O:22][C:23]1[C:32]([CH2:33][CH:34]=O)=[C:31]2[C:26]([C:27](=[O:38])[CH2:28][C:29]([CH3:37])([CH3:36])[O:30]2)=[CH:25][CH:24]=1.O1CCCC1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O.C1(C)C=CC=CC=1.C(O)(=O)C>[CH3:21][O:22][C:23]1[C:32]([CH2:33][CH2:34][N:2]2[CH2:3][CH2:4][CH:5]([N:8]3[C:16]4[C:11](=[CH:12][CH:13]=[C:14]([C:17]([O:19][CH3:20])=[O:18])[CH:15]=4)[CH:10]=[CH:9]3)[CH2:6][CH2:7]2)=[C:31]2[C:26]([C:27](=[O:38])[CH2:28][C:29]([CH3:37])([CH3:36])[O:30]2)=[CH:25][CH:24]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 8028TetrahydrofuranHCID 5049666Sodium triacetoxyborohydrideHCID 57682772(7-Methoxy-2,2-dimethyl-4-oxochroman-8-yl)acetaldehydeHCID 66720891methyl 1-piperidin-4-yl-1H-indole-6-carboxylate hydrochloride

生成物 1

HCID 59439452methyl 1-{1-[2-(7-methoxy-2,2-dimethyl-4-oxochroman-8-yl)ethyl]piperidin-4-yl}-1H-indole-6-carboxylate収率 98.8%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
40 °C

実験手順

2.92 g of methyl 1-piperidin-4-yl-1H-indole-6-carboxylate hydrochloride and 2.92 g of (7-methoxy-2,2-dimethyl-4-oxochroman-8-yl)acetaldehyde were added with 58.4 mL of tetrahydrofuran and 14.6 mL of acetic acid warmed to 40° C. and the reaction mixture was stirred for about 3 hours. The reaction mixture was cooled with an ice-water bath, and 2.52 g of sodium triacetoxyborohydride was added portionwise divided into three. The reaction mixture was warmed to room temperature and 30 minutes later, progress of the reaction was confirmed. The reaction mixture was cooled with an ice-water bath again and 87 mL of toluene and 29 mL of water were added thereto and the aqueous layer was discarded. The organic layer was washed with 49 mL, 69 mL, 30 mL of 1 N aqueous sodium hydroxide sequentially and then with 29 mL, 14 mL of 5% sodium chloride solution and 14 mL of water. The solvent was evaporated and 4.80 g of the crude title compound was obtained.

後処理

  1. temperatureThe reaction mixture was cooled with an ice-water bath
  2. temperatureThe reaction mixture was warmed to room temperature and 30 minutes later
  3. temperatureThe reaction mixture was cooled with an ice-water bath again
  4. washThe organic layer was washed with 49 mL, 69 mL, 30 mL of 1 N aqueous sodium hydroxide sequentially
  5. customThe solvent was evaporated

出典と根拠

ORDレコード
ord-5633f7b5a04e47b28610fabd2a9c1869
出典データセット
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08110688B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート