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6-Bromoisoquinoline → tert-Butyl 8-(isoquinolin-6-yl)-2,8-diazaspiro[4.5]decane-2-carboxylate

HRID 1253703
ノート
印刷プレビュー

反応式

HRID 1253703 の反応式
[CH2:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[CH2:4][CH2:3][N:2]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].Br[C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[CH:25]=[N:24][CH:23]=[CH:22]2.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.[Pd].C([O-])(=O)C>[CH:25]1[C:26]2[C:21](=[CH:20][C:19]([N:8]3[CH2:7][CH2:6][C:5]4([CH2:1][N:2]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:3][CH2:4]4)[CH2:10][CH2:9]3)=[CH:28][CH:27]=2)[CH:22]=[CH:23][N: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

6

反応物 3

HCID 3136816-BromoisoquinolineHCID 634876Binap, (A+-)-HCID 34178604tert-Butyl 2,8-diazaspiro[4.5]decane-2-carboxylate

生成物 1

HCID 66700964tert-Butyl 8-(isoquinolin-6-yl)-2,8-diazaspiro[4.5]decane-2-carboxylate収率 52%

試薬・触媒・溶媒 2

HCID 9793925palladium(I)acetate触媒
HCID 1140
Toluene
溶媒

反応条件

温度
120 °C

実験手順

Sodium t-butylate (6.24 mmol, 3.0 eq.) was added to a solution of tert-butyl 2,8-diazaspiro[4.5]decane-2-carboxylate (2.08 mmol, 1.0 eq.) and 6-bromoisoquinoline (2.08 mmol, 1.0 eq.) in toluene (10 ml) and the reaction mixture was degassed with N2. BINAP (0.124 mmol, 0.06 eq.) and Pd acetate (0.04 mmol, 0.02 eq.) were added and the mixture was heated at 120° C. for 12 h. The reaction mixture was filtered over Celite and the filtrate was concentrated on a rotary evaporator. The crude product was purified by means of column chromatography (silica gel, 5% methanol in methylene chloride) in order to obtain the desired product. Yield: 52%

後処理

  1. customthe reaction mixture was degassed with N2
  2. filtrationThe reaction mixture was filtered over Celite
  3. concentrationthe filtrate was concentrated on a rotary evaporator
  4. customThe crude product was purified by means of column chromatography (silica gel, 5% methanol in methylene chloride) in order

出典と根拠

ORDレコード
ord-3bf872bff1f7480ea9de142df912f99b
出典データセット
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08455475B2

反応ノート

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