(1R,2R,4R,S_S)-N-[(1E)-benzylidene]-2-(2-trimethylsilyloxy-4-methylcyclohexyl)propane-2-sulfinamide

Base Information

• Chemical Name: (1R,2R,4R,S_S)-N-[(1E)-benzylidene]-2-(2-trimethylsilyloxy-4-methylcyclohexyl)propane-2-sulfinamide
• CAS No.: 622840-45-3
• Molecular Formula: C₂₀H₃₃NO₂SSi
• Molecular Weight: 379.639

Synonyms:(1R,2R,4R,S_S)-N-[(1E)-benzylidene]-2-(2-trimethylsilyloxy-4-methylcyclohexyl)propane-2-sulfinamide

Chemical Property of (1R,2R,4R,S_S)-N-[(1E)-benzylidene]-2-(2-trimethylsilyloxy-4-methylcyclohexyl)propane-2-sulfinamide

Chemical Property:

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Technology Process of (1R,2R,4R,S_S)-N-[(1E)-benzylidene]-2-(2-trimethylsilyloxy-4-methylcyclohexyl)propane-2-sulfinamide

There total 1 articles about (1R,2R,4R,S_S)-N-[(1E)-benzylidene]-2-(2-trimethylsilyloxy-4-methylcyclohexyl)propane-2-sulfinamide 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: 92.0%

benzaldehyde (100-52-7) + (1R,2R,4R,SS)-2-(2-trimethylsilyloxy-4-methylcyclohexyl)propane-2-sulfinamide → (1R,2R,4R,SS)-N-[(1E)-benzylidene]-2-(2-trimethylsilyloxy-4-methylcyclohexyl)propane-2-sulfinamide (622840-45-3)

Guidance literature:

With titanium(IV) tetraethanolate; In tetrahydrofuran; at 20 ℃; for 16h;

DOI:10.1016/S0957-4166(03)00624-4

Reference yield: 80.0%

ethylmagnesium bromide (925-90-6) + (1R,2R,4R,SS)-N-[(1E)-benzylidene]-2-(2-trimethylsilyloxy-4-methylcyclohexyl)propane-2-sulfinamide (622840-45-3) → (1R,1'R,2R,4R,SS)-N-(1'-phenylpropyl)-2-(2-trimethylsilyloxy-4-methylcyclohexyl)propane-2-sulfinamide (622840-47-5)

Guidance literature:

In dichloromethane; at -30 ℃; for 3.5h;

DOI:10.1016/S0957-4166(03)00624-4

Reference yield:

(1R,2R,4R,SS)-N-[(1E)-benzylidene]-2-(2-trimethylsilyloxy-4-methylcyclohexyl)propane-2-sulfinamide (622840-45-3) → (R)-1-phenylpropan-1-amine hydrochloride (19068-33-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / CH₂Cl₂ / 3.5 h / -30 °C

2: HCl*Et₂O / diethyl ether / 0.5 h

With hydrochloric acid diethyl ether; In diethyl ether; dichloromethane;

DOI:10.1016/S0957-4166(03)00624-4

upstream raw materials:

benzaldehyde

Downstream raw materials:

(1R,1'R,2R,4R,S_S)-N-(1'-phenylpropyl)-2-(2-trimethylsilyloxy-4-methylcyclohexyl)propane-2-sulfinamide

(R)-1-phenylpropan-1-amine hydrochloride

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