ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Lithium borohydride → tert-Butyl N-[(1R,2S)-rel-2-(4-hydroxyphenyl)cyclopropyl]carbamate

HRID 1844243
ノート
印刷プレビュー

反応式

HRID 1844243 の反応式
[Li+].[BH4-].C([O:6][C:7]1[CH:12]=[CH:11][C:10]([C@@H:13]2[CH2:15][C@H:14]2[NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:9][CH:8]=1)C=C>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:6][C:7]1[CH:12]=[CH:11][C:10]([C@@H:13]2[CH2:15][C@H:14]2[NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[CH:9][CH:8]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 4148881Lithium borohydrideHCID 86672577Tert-butyl(trans)-2-[4-(allyloxy)phenyl]cyclopropylcarbamate2 回

生成物 1

HCID 86672576tert-Butyl N-[(1R,2S)-rel-2-(4-hydroxyphenyl)cyclopropyl]carbamate収率 90%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8028
Tetrahydrofuran
溶媒

実験手順

LiBH4 (0.34 g, 15.54 mmol) was added to a solution of Pd(PPh3)4 (0.15 g, 0.13 mmol) and tert-butyl(trans)-2-[4-(allyloxy)phenyl]cyclopropylcarbamate (Intermediate I, 0.75 g, 2.59 mmol) in dry THF (20 mL) and stirred at room temperature for 1 h. After removal of the solvent, the residue was dissolved in EtOAc (25 mL), acidified with HCl (10% aqueous solution, 2 mL), and washed with water (25 mL) and brine (25 mL). The organic layer was dried over anhydrous Na2SO4 and filtered. After removal of the solvent, the residue was purified by column chromatography on silica gel (10%-20% EtOAc/Hexanes), affording 0.58 g of tert-butyl(trans)-2-(4-hydroxyphenyl)cyclopropylcarbamate [Rf=0.3 (30% EtOAc/Hexanes), pale yellow foam, 90% yield].

後処理

  1. customAfter removal of the solvent
  2. dissolutionthe residue was dissolved in EtOAc (25 mL)
  3. washwashed with water (25 mL) and brine (25 mL)
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customAfter removal of the solvent
  7. customthe residue was purified by column chromatography on silica gel (10%-20% EtOAc/Hexanes)

出典と根拠

ORDレコード
ord-7efc1b8a183d4426bc66494227fa2af6
出典データセット
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08946296B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート