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Tetrahydrofuran → tert-Butyl 4-((4'-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-(1,1'-biphenyl)-2-yl)methyl)piperazine-1-carboxylate

HRID 591219
ノート
印刷プレビュー

反応式

HRID 591219 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][C:12]([CH3:15])([CH3:14])[CH2:11][CH2:10][C:9]=2[CH:16]=O)=[CH:4][CH:3]=1.[C:18]([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].C1COCC1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH2:13][C:12]([CH3:14])([CH3:15])[CH2:11][CH2:10][C:9]=2[CH2:16][N:28]2[CH2:27][CH2:26][N:25]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:30][CH2:29]2)=[CH:6][CH:7]=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 4

HCID 8028TetrahydrofuranHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 872794142-(4-Chlorophenyl)-4,4-dimethyl-1-cyclohexene-1-carboxaldehyde

生成物 1

HCID 66713018tert-Butyl 4-((4'-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-(1,1'-biphenyl)-2-yl)methyl)piperazine-1-carboxylate

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
20 °C

実験手順

To a 2 L three neck RB flask provided with a mechanical stirrer were charged a solution of 4′-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1′-biphenyl]-2-carbaldehyde (50.0 g) in toluene (250 mL), BOC-piperazine (48.2 g) and anhydrous THF (250 mL). The yellow solution was stirred at 20° C. for 5 min. Sodium triacetoxyborohydride (52.7 g) was added in portion (note: the internal temperature rose to ˜29.5° C. in 15 min cooling may be needed). The yellow mixture was stirred at ˜25° C. for NLT 4 hrs. A conversion of starting material to product of 99.5% was observed by HPLC after a 3 hour reaction time.

後処理

  1. waitthe internal temperature rose to ˜29.5° C. in 15 min
  2. temperaturecooling may
  3. stirringThe yellow mixture was stirred at ˜25° C. for NLT 4 hrs
  4. waitA conversion of starting material to product of 99.5% was observed by HPLC after a 3 hour
  5. customreaction time

出典と根拠

ORDレコード
ord-b2e8ef7080414b58b2f09ddbb63c999d
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09238652B2

反応ノート

読み込み中…

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