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

HRID 129424
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HRID 129424 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
참가 물질실험 절차후처리출처 및 근거반응 노트

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 Z23, method II) are stirred overnight at room temperature in 166 ml of trifluoroacetic acid. The trifluoroacetic acid is then distilled off at 10 mbar, and the residue is freed from remaining acid in a high vacuum at 50° C. The residue is subsequently taken up in absolute tetrahydrofuran and concentrated in vacuo. The residue is taken up in 100 ml of absolute tetrahydrofuran and the mixture is added dropwise under nitrogen to a solution of 11.3 g (0.3 mol) of lithium aluminium hydride in 300 ml of absolute tetrahydrofuran. The mixture is then refluxed for 16 hours. 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 to the cold mixture. 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 at 10 mbar
  2. customat 50° C
  3. concentrationconcentrated in vacuo
  4. temperatureThe mixture is then refluxed for 16 hours
  5. filtrationThe precipitate is filtered off with suction
  6. washwashed with tetrahydrofuran
  7. concentrationThe filtrate is concentrated
  8. distillationthe residue is distilled

출처 및 근거

ORD 기록
ord-d5143bddb73f4f73932db5b10f919d77
출처 데이터셋
uspto-grants-1995_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05468742

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