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Water → 4-Amino-1,3,3a,4,7,7a-hexahydro-isoindole

HRID 128516
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HRID 128516 반응식
C(OC([NH:8][CH:9]1[CH:17]=[CH:16][CH2:15][CH:14]2[CH:10]1[C:11](=O)[NH:12][C:13]2=O)=O)(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>FC(F)(F)C(O)=O.O1CCCC1>[NH2:8][CH:9]1[CH:17]=[CH:16][CH2:15][CH:14]2[CH:10]1[CH2:11][NH:12][CH2:13]2
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참가 물질

7

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 193714494-(Tert.-butyloxycarbonylamino)-1,3-dioxo-1,3,3a,4,7,7a-hexahydroisoindoleHCID 21226445Aluminium lithium hydride

생성물 1

HCID 152832494-Amino-1,3,3a,4,7,7a-hexahydro-isoindole

시약·촉매·용매 2

HCID 6422
Trifluoroacetic acid
용매
HCID 8028Tetrahydrofuran용매2회

실험 절차

13.3 g (50 mmol) of 4-tert.-butyloxycarbonylamino-1,3-dioxo-1,3,3a,4,7,7a-hexahydro-isoindole (from Example A, method II) are stirred in 166 ml of trifluoroacetic acid at room temperature overnight. The trifluoroacetic acid is then distilled off under 10 mbar and the residue is freed from residues of acid at 50° under a high vacuum. It is then taken up in absolute tetrahydrofuran and the mixture is concentrated in vacuo. The residue is taken up in 100 ml of absolute tetrahydrofuran and the mixture is added dropwise to a solution of 11.3 g (0.3 mol) of lithium aluminium hydride in 300 ml of absolute tetrahydrofuran, under nitrogen. The mixture is then boiled under reflux cooling for 16 hours. After cooling, 11.3 g of water in 34 ml of tetrahydrofuran, 11.3 ml of 10% strength sodium hydroxide solution and 34 ml of water are added dropwise in succession. The precipitate is filtered off with suction and washed with tetrahydrofuran. The filtrate is concentrated and the residue is distilled.

후처리

  1. distillationThe trifluoroacetic acid is then distilled off under 10 mbar
  2. customis freed from residues of acid at 50° under a high vacuum
  3. concentrationthe mixture is concentrated in vacuo
  4. temperatureunder reflux
  5. temperaturecooling for 16 hours
  6. temperatureAfter cooling
  7. filtrationThe precipitate is filtered off with suction
  8. washwashed with tetrahydrofuran
  9. concentrationThe filtrate is concentrated
  10. distillationthe residue is distilled

출처 및 근거

ORD 기록
ord-ee0ea68cb44f437db786bfc02b6bc26f
출처 데이터셋
uspto-grants-1995_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05464796

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