(4bS,8R,8aS,9aR,10S,13aR,13bR)-10-tert-butyl-7-cyclopropylmethyl-5,6,7,8,9,9a,10,13b-octahydro-10-methyl-8a,13a-ethano-4,8-methanobenzofuro[3,2-e][1,3]dioxino[4,5-g]isoquinolin-1-ol → (4bS,8R,8aR,9aR,10S,13aR,13bR)-7-allyl-10-tert-butyl-5,6,7,8,9,9a,10,13b-octahydro-10-methyl-8a,13a-ethano-4,8-methanobenzofuro[3,2-e][1,3]dioxino[4,5-g]isoquinolin-1-ol

HRID 629836Notes

Reaction equation

HRID 629836 reaction equation
[C:1]([C@:5]1([CH3:34])[C@@H:18]2[C@@:9]3([CH2:20][CH2:19][C@:16]4([CH2:17]2)[C@@:11]25[C:27]6[C:22](=[CH:23][CH:24]=[C:25]([OH:29])[C:26]=6[O:28][C@@H:10]32)[CH2:21][C@H:15]4[N:14]([CH2:30][CH:31]2C[CH2:32]2)[CH2:13][CH2:12]5)[O:8][CH2:7][O:6]1)([CH3:4])([CH3:3])[CH3:2].C(N1CC[C@@]23C4C5C[C@@H]1[C@H]2C[C@H]([C@](O)(C(C)(C)C)C)[C@H](O)[C@@H]3OC=4C(O)=C1CCC1=5)C=C.C1(CN2CC[C@@]34C5C6C[C@@H]2[C@H]3C[C@H]([C@](O)(C(C)(C)C)C)[C@H](O)[C@@H]4OC=5C(O)=C2CCC2=6)CC1>>[CH2:30]([N:14]1[CH2:13][CH2:12][C@@:11]23[C:27]4[C:22]5[CH2:21][C@@H:15]1[C@:16]12[CH2:19][CH2:20][C@:9]2([O:8][CH2:7][O:6][C@@:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:34])[C@H:18]2[CH2:17]1)[C@@H:10]3[O:28][C:26]=4[C:25]([OH:29])=[CH:24][CH:23]=5)[CH:31]=[CH2:32]

Participants

4

Reactant 3

HCID 73211769(4bS,8R,8aS,9aR,10S,13aR,13bR)-10-tert-butyl-7-cyclopropylmethyl-5,6,7,8,9,9a,10,13b-octahydro-10-methyl-8a,13a-ethano-4,8-methanobenzofuro[3,2-e][1,3]dioxino[4,5-g]isoquinolin-1-olHCID 8671165917-cyclopropylmethyl-7alpha-[(2S)-3,3-dimethyl-2-hydroxybutan-2-yl]-4,5alpha-epoxy-3,6-dihydroxy-6alpha,14alpha-ethanomorphinanHCID 8671166317-allyl-7alpha-[(2S)-3,3-dimethyl-2-hydroxybutan-2-yl]-4,5alpha-epoxy-3,6-dihydroxy-6alpha,14alpha-ethanomorphinan

Product 1

HCID 86711664(4bS,8R,8aR,9aR,10S,13aR,13bR)-7-allyl-10-tert-butyl-5,6,7,8,9,9a,10,13b-octahydro-10-methyl-8a,13a-ethano-4,8-methanobenzofuro[3,2-e][1,3]dioxino[4,5-g]isoquinolin-1-olYield 49%

Procedure

The title compound 17 was synthesized similar to the procedure described in Example 1 for preparing compound 3 using compound 16 rather than compound 2. After column chromatography, 1.29 g (49.0% yield) of compound 17 was isolated in a purity of >99% as a-white solid.

Workup

  1. customThe title compound 17 was synthesized similar to the procedure

Sources & evidence

ORD record
ord-6ec913134b814e89a44410f7a60fc59e
Source dataset
uspto-grants-2016_04
Patent number
US09315514B2

Reaction notes

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