Dibutyl sulfoxide → (4bS,8R,8aS,9aR,10S,13aR,13bR)-10-tert-butyl-7-cyclopropylmethyl-5,6,7,8,9,9a,10,13b-octahydro-10-methyl-12-propyl-8a,13a-ethano-4,8-methanobenzofuro[3,2-e][1,3]dioxino[4,5-g]isoquinolin-1-ol

HRID 629831Notes

Reaction equation

HRID 629831 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]2[CH2:33][CH2:32]2)[CH2:13][CH2:12]5)[O:8][CH2:7][O:6]1)([CH3:4])([CH3:3])[CH3:2].[CH2:35](S(CCCC)=O)[CH2:36][CH2:37]C>>[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]2[CH2:32][CH2:33]2)[CH2:13][CH2:12]5)[O:8][CH:7]([CH2:35][CH2:36][CH3:37])[O:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 16568Dibutyl sulfoxideHCID 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-ol

Product 1

HCID 89984906(4bS,8R,8aS,9aR,10S,13aR,13bR)-10-tert-butyl-7-cyclopropylmethyl-5,6,7,8,9,9a,10,13b-octahydro-10-methyl-12-propyl-8a,13a-ethano-4,8-methanobenzofuro[3,2-e][1,3]dioxino[4,5-g]isoquinolin-1-ol

Procedure

The title compound 5 was synthesized similar to the procedure described in Example 1 for compound 3 using dibutyl sulfoxide instead of DMSO. After column chromatography, 227 mg (86.3% yield, 99.4 purity) of compound 5 was isolated as an off-white solid as a mixture of two epimers in a 95.4:4.6 ratio.

Workup

  1. customThe title compound 5 was synthesized similar to the procedure

Sources & evidence

ORD record
ord-7a27baa4a6a845e18358cac6be428235
Source dataset
uspto-grants-2016_04
Patent number
US09315514B2

Reaction notes

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