(3R,3aR,7aS)-4-(tert-butyldiphenylsilyloxy)-3-(1-oxooctahydroisoindol-2-yl)butyronitrile

Base Information

Chemical Name:(3R,3aR,7aS)-4-(tert-butyldiphenylsilyloxy)-3-(1-oxooctahydroisoindol-2-yl)butyronitrile
CAS No.:260391-27-3
Molecular Formula:C₂₈H₃₆N₂O₂Si
Molecular Weight:460.692
Hs Code.:

Synonyms:(3R,3aR,7aS)-4-(tert-butyldiphenylsilyloxy)-3-(1-oxooctahydroisoindol-2-yl)butyronitrile

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Chemical Property of (3R,3aR,7aS)-4-(tert-butyldiphenylsilyloxy)-3-(1-oxooctahydroisoindol-2-yl)butyronitrile

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Technology Process of (3R,3aR,7aS)-4-(tert-butyldiphenylsilyloxy)-3-(1-oxooctahydroisoindol-2-yl)butyronitrile

There total 8 articles about (3R,3aR,7aS)-4-(tert-butyldiphenylsilyloxy)-3-(1-oxooctahydroisoindol-2-yl)butyronitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 41.0%

: (3R)-4-(tert-butyldiphenylsilyloxy)-3-(1-hydroxy-3-oxooctahydroisoindol-2-yl)butyronitrile

: 260391-28-4
(3R,3aS,7aR)-4-(tert-butyldiphenylsilyloxy)-3-(1-oxooctahydroisoindol-2-yl)butyronitrile

: 260391-27-3
(3R,3aR,7aS)-4-(tert-butyldiphenylsilyloxy)-3-(1-oxooctahydroisoindol-2-yl)butyronitrile

Guidance literature:: With triethylsilane; trifluoroacetic acid; In dichloromethane; at -15 ℃; for 2h;
DOI:10.1002/(sici)1099-0690(200001)2000:1<115::aid-ejoc115>3.0.co;2-j

Reference yield:

: 159846-14-7
methyl (2S)-3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)-2-[(tert-butoxy)carbonylamino]propanoate

: 260391-27-3
(3R,3aR,7aS)-4-(tert-butyldiphenylsilyloxy)-3-(1-oxooctahydroisoindol-2-yl)butyronitrile

Guidance literature:: Multi-step reaction with 7 steps

1: 68 percent / LiBH₄ / diethyl ether / 1 h / 0 - 20 °C

2: 96 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

3: 72 percent / 18-crown-6 / acetonitrile / 2 h / Heating

4: 100 percent / trifluoroacetic acid / 1 h / 0 °C

5: 30 percent / 0.17 h / 200 °C

6: 95 percent / NaBH₄; H₂SO₄ / ethanol / 1.5 h / -15 °C

7: 41 percent / trifluoroacetc acid; triethylsilane / CH₂Cl₂ / 2 h / -15 °C

With triethylsilane; sodium tetrahydroborate; lithium borohydride; 18-crown-6 ether; sulfuric acid; triethylamine; trifluoroacetic acid; In diethyl ether; ethanol; dichloromethane; acetonitrile; 1: Reduction / 2: Condensation / 3: Substitution / 4: deprotection / 5: Condensation / 6: Reduction / 7: Reduction;
DOI:10.1002/(sici)1099-0690(200001)2000:1<115::aid-ejoc115>3.0.co;2-j

Reference yield:

: 198417-69-5
tert-butyl [(1R)-2-(tert-butyldiphenylsilyloxy)-1-(hydroxymethyl)-ethyl]carbamate

: 260391-27-3
(3R,3aR,7aS)-4-(tert-butyldiphenylsilyloxy)-3-(1-oxooctahydroisoindol-2-yl)butyronitrile

Guidance literature:: Multi-step reaction with 6 steps

1: 96 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

2: 72 percent / 18-crown-6 / acetonitrile / 2 h / Heating

3: 100 percent / trifluoroacetic acid / 1 h / 0 °C

4: 30 percent / 0.17 h / 200 °C

5: 95 percent / NaBH₄; H₂SO₄ / ethanol / 1.5 h / -15 °C

6: 41 percent / trifluoroacetc acid; triethylsilane / CH₂Cl₂ / 2 h / -15 °C

With triethylsilane; sodium tetrahydroborate; 18-crown-6 ether; sulfuric acid; triethylamine; trifluoroacetic acid; In ethanol; dichloromethane; acetonitrile; 1: Condensation / 2: Substitution / 3: deprotection / 4: Condensation / 5: Reduction / 6: Reduction;
DOI:10.1002/(sici)1099-0690(200001)2000:1<115::aid-ejoc115>3.0.co;2-j