HCID 117857475, compound → HCID 117857410, compound

HRID 1483161Notes

Reaction equation

HRID 1483161 reaction equation
[CH:1]1([CH2:5][N:6]2[CH2:19][CH2:18][C@@:17]34[C:20]5[C:26]6[CH2:27][C@@H:7]2[C@@H:8]3[CH2:9][CH2:10][C:11]2([C@@H:16]4[O:22][C:21]=5[C:23]([C:28]#[N:29])=[CH:24][CH:25]=6)OCC[O:12]2)[CH2:4][CH2:3][CH2:2]1>Cl>[CH:1]1([CH2:5][N:6]2[CH2:19][CH2:18][C@@:17]34[C:20]5[C:26]6[CH2:27][C@@H:7]2[C@@H:8]3[CH2:9][CH2:10][C:11](=[O:12])[C@@H:16]4[O:22][C:21]=5[C:23]([C:28]#[N:29])=[CH:24][CH:25]=6)[CH2:2][CH2:3][CH2:4]1

Participants

3

Reactant 1

HCID 117857475HCID 117857475, compound

Product 1

HCID 117857410HCID 117857410, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

A suspension of (4R,4aR,7aR,12bS)-3-(cyclobutylmethyl)-1,2,3,4,4a,5,6,7a-octahydrospiro[4,12-methanobenzofuro[3,2-e]isoquinoline-7,2′-[1,3]dioxolane]-9-carbonitrile (31.1 g, 79.2 mmol) in 6M HCl(aq) (250 mL) was stirred at room temperature at room temperature for 24 hours. Further 6M HCl was added (25 mL) and stirred for an additional 24 hours. The reaction was poured onto ice/NH3(aq) and stirred for 30 minutes and the solid collected by suction filtration and washed with water. The solid was dissolved in dichloromethane and washed with brine, dried over MgSO4 and concentrated under reduced pressure to give (4R,4aR,7aR,12bS)-3-(cyclobutylmethyl)-7-oxo-2,3,4,4a,5,6,7,7a-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-9-carbonitrile (26.1 g, 96% pure LCMS, 95% yield); [M+H]+ 367.2.

Workup

  1. stirringstirred for an additional 24 hours
  2. additionThe reaction was poured onto ice/NH3(aq)
  3. stirringstirred for 30 minutes
  4. filtrationthe solid collected by suction filtration
  5. washwashed with water
  6. dissolutionThe solid was dissolved in dichloromethane
  7. washwashed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d62b867064da438a865c3aa980d4c605
Source dataset
uspto-grants-2016_08
Patent number
US09416137B2

Reaction notes

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