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

HRID 629837Notes

Reaction equation

HRID 629837 reaction equation
[CH2:1]([O:8][C:9]1[C:14]2[O:15][C@H:16]3[C@@:25]45[CH2:35][CH2:36][C@:22]6([CH2:23][C@@H:24]4[C@:29]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[O:28][CH2:27][O:26]5)[C@@:17]43[CH2:18][CH2:19][N:20]([CH2:38][CH:39]3C[CH2:40]3)[C@@H:21]6[CH2:37][C:12]([C:13]=24)=[CH:11][CH:10]=1)C1C=CC=CC=1.CI.C(Br)C1C=CC=CC=1.C(N1CC[C@@]23C4C5C[C@@H]1[C@]12CC[C@]2(OCO[C@@](C(C)(C)C)(C)[C@H]2C1)[C@@H]3OC=4C(O)=CC=5)C=C.C([C@]1(C)[C@@H]2[C@@]3(CC[C@]4(C2)[C@@]25C6C(=CC=C(O)C=6O[C@@H]32)C[C@H]4N(CC2CC2)CC5)OCO1)(C)(C)C>>[CH2:38]([N:20]1[CH2:19][CH2:18][C@@:17]23[C:13]4[C:12]5[CH2:37][C@@H:21]1[C@:22]12[CH2:36][CH2:35][C@:25]2([O:26][CH2:27][O:28][C@@:29]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[C@H:24]2[CH2:23]1)[C@@H:16]3[O:15][C:14]=4[C:9]([O:8][CH3:1])=[CH:10][CH:11]=5)[CH:39]=[CH2:40]

Participants

6

Reactant 5

HCID 6328Methyl iodideHCID 7498Benzyl BromideHCID 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 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-olHCID 121278739(4bS,8R,8aS,9aR,10S,13aR,13bR)-1-benzyloxy-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]isoquinoline

Product 1

HCID 86711665(4bS,8R,8aR,9aR,10S,13aR,13bR)-7-allyl-10-tert-butyl-5,6,7,8,9,9a,10,13b-octahydro-1-methoxy-10-methyl-8a,13a-ethano-4,8-methanobenzofuro[3,2-e][1,3]dioxino[4,5-g]isoquinolineYield 58%

Procedure

The title compound 18 was synthesized similar to the procedure described in Example 5 for preparing compound 7 using methyl iodide rather than benzyl bromide and compound 17 rather than compound 3. After column chromatography, 300 mg (58% yield) of compound 18 was isolated in a purity of >99% as a white solid.

Workup

  1. customThe title compound 18 was synthesized similar to the procedure

Sources & evidence

ORD record
ord-9f2a354440954d5e9df8b2c0faf28f1e
Source dataset
uspto-grants-2016_04
Patent number
US09315514B2

Reaction notes

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