Buprenorphine component OF alks-5461 → 17-allyl-7alpha-[(2S)-3,3-dimethyl-2-hydroxybutan-2-yl]-4,5alpha-epoxy-3,6-dihydroxy-6alpha,14alpha-ethanomorphinan

HRID 629835Notes

Reaction equation

HRID 629835 reaction equation
[CH:1]1([CH2:4][N:5]2[CH2:25][CH2:24][C@@:12]34[C:13]5[C:18]6[CH2:19][C@@H:6]2[C@H:7]3[CH2:8][C@H:9]([C@:27]([OH:33])([C:29]([CH3:32])([CH3:31])[CH3:30])[CH3:28])[C@H:10]([OH:26])[C@@H:11]4[O:23][C:14]=5[C:15]([OH:22])=[C:16]2[CH2:21][CH2:20][C:17]2=6)C[CH2:2]1.C(N1CC[C@@]23C4C5C[C@@H]1[C@H]2C[C@H]([C@](O)(C(C)(C)C)C)[C@H](OC)[C@@H]3OC=4C(O)=C1CCC1=5)C=C.C[C@@](O)(C(C)(C)C)[C@@H]1[C@]2(OC)[C@@H]3OC4=C(O)C=CC5=C4[C@]43CCN(CC3CC3)[C@H](C5)[C@@]4(CC2)C1>>[CH2:4]([N:5]1[CH2:25][CH2:24][C@@:12]23[C:13]4[C:18]5[CH2:19][C@@H:6]1[C@H:7]2[CH2:8][C@H:9]([C@:27]([OH:33])([C:29]([CH3:32])([CH3:31])[CH3:30])[CH3:28])[C@H:10]([OH:26])[C@@H:11]3[O:23][C:14]=4[C:15]([OH:22])=[C:16]1[CH2:21][CH2:20][C:17]1=5)[CH:1]=[CH2:2]

Participants

4

Reactant 3

HCID 9848990Buprenorphine component OF alks-5461HCID 8671165917-cyclopropylmethyl-7alpha-[(2S)-3,3-dimethyl-2-hydroxybutan-2-yl]-4,5alpha-epoxy-3,6-dihydroxy-6alpha,14alpha-ethanomorphinanHCID 8671166217-allyl-7alpha-[(2S)-3,3-dimethyl-2-hydroxybutan-2-yl]-4,5alpha-epoxy-3-hydroxy-6-methoxy-6alpha,14alpha-ethanomorphinan

Product 1

HCID 8671166317-allyl-7alpha-[(2S)-3,3-dimethyl-2-hydroxybutan-2-yl]-4,5alpha-epoxy-3,6-dihydroxy-6alpha,14alpha-ethanomorphinanYield 75.8%

Procedure

Compound 16 was synthesized similar to the procedure described in Example 1 for the preparation of compound 2 using compound 15 rather than compound 1. After column chromatography, 4.0 g of compound 16 (75.8%) was obtained with a purity of 98.5%.

Workup

  1. customCompound 16 was synthesized similar to the procedure

Sources & evidence

ORD record
ord-fde15df01f84463c9c11d56a4c5b73fe
Source dataset
uspto-grants-2016_04
Patent number
US09315514B2

Reaction notes

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