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Sodium Hydroxide → ((1R,3R)-1-amino-3-(4-(3-(benzyloxy)prop-1-ynyl)phenyl)cyclopentyl)methanol

HRID 1511852
ノート
印刷プレビュー

反応式

HRID 1511852 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH2:7][C@:8]1([C:30](OC)=[O:31])[CH2:12][CH2:11][C@@H:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]#[C:20][CH2:21][O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:15][CH:14]=2)[CH2:9]1.[OH-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>CCOCC.C1COCC1.O>[NH2:7][C@:8]1([CH2:30][OH:31])[CH2:12][CH2:11][C@@H:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]#[C:20][CH2:21][O:22][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[CH:15][CH:14]=2)[CH2:9]1
参加物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 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 57554604(1R,3R)-methyl 1-amino-3-(4-(3-(benzyloxy)prop-1-ynyl)phenyl)cyclopentanecarboxylate

生成物 1

HCID 57554621((1R,3R)-1-amino-3-(4-(3-(benzyloxy)prop-1-ynyl)phenyl)cyclopentyl)methanol収率 81.3%

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回
HCID 3283Diethyl Ether溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

To a slurry of LAH (7.83 g, 206 mmol) in Et2O (500 mL) at about 0° C. was added a solution of (1R,3R)-methyl 1-amino-3-(4-(3-(benzyloxy)prop-1-ynyl)phenyl)cyclopentanecarboxylate (25 g, 68.8 mmol) in THF (100 mL). After about 2 hours water (7.8 mL) followed by 2N NaOH (7.8 mL) followed by water (15 mL) was added. After stirring for about 15 hours Na2SO4 and Celite® was added to the reaction mixture and the slurry was filtered, rinsing with EtOAc. The filtrate was concentrated in vacuo to provide ((1R,3R)-1-amino-3-(4-(3-(benzyloxy)prop-1-ynyl)phenyl)cyclopentyl)methanol (25 g, 55.9 mmol, 81% yield) as an brown oil.

後処理

  1. additionwas added
  2. additionwas added to the reaction mixture
  3. filtrationthe slurry was filtered
  4. washrinsing with EtOAc
  5. concentrationThe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-9dd0a2339ffa462d8a88678bc9f8a79b
出典データセット
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08217027B2

反応ノート

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