(1S)-1-[[2S(2α,4aα,7α,8aβ)]-3-allyl-4,4,7-trimethyl-octahydrobenzo[e][1,3]oxazin-2-yl]-1-phenyl-pent-4-en-1-ol

Base Information

• Chemical Name: (1S)-1-[[2S(2α,4aα,7α,8aβ)]-3-allyl-4,4,7-trimethyl-octahydrobenzo[e][1,3]oxazin-2-yl]-1-phenyl-pent-4-en-1-ol
• CAS No.: 862553-54-6
• Molecular Formula: C₂₅H₃₇NO₂
• Molecular Weight: 383.574

Synonyms:(1S)-1-[[2S(2α,4aα,7α,8aβ)]-3-allyl-4,4,7-trimethyl-octahydrobenzo[e][1,3]oxazin-2-yl]-1-phenyl-pent-4-en-1-ol

Chemical Property of (1S)-1-[[2S(2α,4aα,7α,8aβ)]-3-allyl-4,4,7-trimethyl-octahydrobenzo[e][1,3]oxazin-2-yl]-1-phenyl-pent-4-en-1-ol

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Technology Process of (1S)-1-[[2S(2α,4aα,7α,8aβ)]-3-allyl-4,4,7-trimethyl-octahydrobenzo[e][1,3]oxazin-2-yl]-1-phenyl-pent-4-en-1-ol

There total 2 articles about (1S)-1-[[2S(2α,4aα,7α,8aβ)]-3-allyl-4,4,7-trimethyl-octahydrobenzo[e][1,3]oxazin-2-yl]-1-phenyl-pent-4-en-1-ol 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%

(2S,4aS,7R,8aR)-N-allyl-2-benzoyl-4,4,7-trimethyl-octahydrobenzo[e][1,3]oxazine (848033-71-6) + 4-but-1-enylmagnesium bromide (7103-09-5) → (1S)-1-[[2S(2α,4aα,7α,8aβ)]-3-allyl-4,4,7-trimethyl-octahydrobenzo[e][1,3]oxazin-2-yl]-1-phenyl-pent-4-en-1-ol (862553-54-6) + (1R)-1-[[2S(2α,4aα,7α,8aβ)]-3-allyl-4,4,7-trimethyl-octahydrobenzo[e][1,3]oxazin-2-yl]-1-phenyl-pent-4-en-1-ol

Guidance literature:

In diethyl ether; at -10 ℃;

DOI:10.1002/ejoc.200400836

Reference yield:

(2S,4aS,7R,8aR)-phenyl-[4,4,7-trimethyloctahydrobenzo[e][1,3]oxazin-2-yl] ketone (503004-87-3) → (1S)-1-[[2S(2α,4aα,7α,8aβ)]-3-allyl-4,4,7-trimethyl-octahydrobenzo[e][1,3]oxazin-2-yl]-1-phenyl-pent-4-en-1-ol (862553-54-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / potassium carbonate / acetonitrile / 80 - 90 °C

2: 92 percent / diethyl ether / -10 °C

With potassium carbonate; In diethyl ether; acetonitrile;

DOI:10.1002/ejoc.200400836

Reference yield: 68.0%

(1S)-1-[[2S(2α,4aα,7α,8aβ)]-3-allyl-4,4,7-trimethyl-octahydrobenzo[e][1,3]oxazin-2-yl]-1-phenyl-pent-4-en-1-ol (862553-54-6) → (3R,4aR,5aS,6S,12aS)-6-phenyl-3,12,12-trimethyl-2,3,4,4a,6,7,8,11,12,12a-decahydro-1H,5aH-5-oxa-11a-azacycloocta[b]naphthalen-6-ol

Guidance literature:

Grubbs catalyst first generation; In benzene; for 30h; Heating;

DOI:10.1002/ejoc.200400836

upstream raw materials:

(2S,4aS,7R,8aR)-N-allyl-2-benzoyl-4,4,7-trimethyl-octahydrobenzo[e][1,3]oxazine

4-but-1-enylmagnesium bromide

(2S,4aS,7R,8aR)-phenyl-[4,4,7-trimethyloctahydrobenzo[e][1,3]oxazin-2-yl] ketone

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