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Sodium Hydroxide → (1S,4S)-4-amino-1,2,3,4-tetrahydronaphthalen-1-ol

HRID 572063
ノート
印刷プレビュー

反応式

HRID 572063 の反応式
FC(F)(F)C([NH:5][C@@H:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C@@H:9]([OH:16])[CH2:8][CH2:7]1)=O.[OH-].[Na+]>CO.O.C(Cl)Cl>[NH2:5][C@@H:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C@@H:9]([OH:16])[CH2:8][CH2:7]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 14798Sodium Hydroxide2 回HCID 866866812,2,2-Trifluoro-N-((1S,4S)-4-hydroxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-acetamide

生成物 1

HCID 86686682(1S,4S)-4-amino-1,2,3,4-tetrahydronaphthalen-1-ol収率 84%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒
HCID 6344
Dichloromethane
溶媒

実験手順

To a grey solution of Intermediate 5a (5.55 g, 21.4 mmol) in MeOH (50 mL), NaOH (1.28 g, 32.1 mmol) in water (15 mL) was added, and the mixture stirred at room temperature for 3 days. NaOH (1.28 g, 32.1 mmol) was further added and the brown solution was stirred for 5 h. The solution was applied directly to an SCX-2 column, washing with MeOH and eluting with 2M NH3 in MeOH, and concentrated under vacuum to leave a grey solid. The solid was suspended in DCM (50 mL) with sonication, then filtered and dried under vacuum to leave a pale grey solid (2.93 g, 84%). 1H NMR (400 MHz, d6-DMSO): 1.41-1.64 (2H, m), 2.02-2.13 (2H, m), 3.82 (1H, dd), 4.55 (1H, dd), 5.08 (1H, br s), 7.13-7.22 (2H, m), 7.35-7.49 (2H, m).

後処理

  1. stirringthe brown solution was stirred for 5 h
  2. washwashing with MeOH
  3. washeluting with 2M NH3 in MeOH
  4. concentrationconcentrated under vacuum
  5. customto leave a grey solid
  6. filtrationfiltered
  7. customdried under vacuum

出典と根拠

ORDレコード
ord-9ee467118cf84132869d74a1f9be267f
出典データセット
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09029373B2

反応ノート

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