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

HRID 572063
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HRID 572063 반응식
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
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참가 물질

6

반응물 2

HCID 14798Sodium Hydroxide2회HCID 866866812,2,2-Trifluoro-N-((1S,4S)-4-hydroxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-acetamide

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매
HCID 6344
Dichloromethane
용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9ee467118cf84132869d74a1f9be267f
출처 데이터셋
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09029373B2

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