Sodium Bicarbonate → tert-Butyl 4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)-1,4-diazepane-1-carboxylate

HRID 1807747ノート

反応式

HRID 1807747 の反応式
[N:1]1([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([OH:32])([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=1.C(=O)([O-])O.[Na+]>C(#N)C>[F:25][C:24]([F:26])([F:27])[C:23]([C:20]1[CH:21]=[CH:22][C:17]([CH2:16][N:4]2[CH2:5][CH2:6][CH2:7][N:1]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:2][CH2:3]2)=[CH:18][CH:19]=1)([OH:32])[C:28]([F:29])([F:31])[F:30]

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylateHCID 235273962-[4-(Bromomethyl)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol

生成物 1

HCID 86638560tert-Butyl 4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)-1,4-diazepane-1-carboxylate収率 63.4%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of tert-butyl 1,4-diazepane-1-carboxylate (24.52 mmol, 4.91 g), 2-(4-(bromomethyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (24.52 mmol, 8.26 g) and sodium hydrogencarbonate (36.8 mmol, 3.09 g) in acetonitrile (100 mL) was stirred for 24 hours then was concentrated under reduced pressure. Dichloromethane was added and the suspension was filtered. The filtrate was concentrated under reduced pressure. The residue was chromatographed on silica eluting with dichloromethane to dichloromethane/methanol (5%) to give the title compound (7.1 g). MS (ESI) m/z 457.2 [M+H]+

後処理

  1. concentrationthen was concentrated under reduced pressure
  2. additionDichloromethane was added
  3. filtrationthe suspension was filtered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue was chromatographed on silica eluting with dichloromethane to dichloromethane/methanol (5%)

出典と根拠

ORDレコード
ord-3c9b728cc4a94539b578c54ab3790306
出典データセット
uspto-grants-2013_01
特許番号
US08357679B2

反応ノート

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