Water → HCID 86725258, compound

HRID 576625Notes

Reaction equation

HRID 576625 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][N:8]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH2:7]2)[CH:2]=[CH2:3].C[N+]1([O-])CC[O:27]CC1.[OH2:31]>C(O)(C)(C)C.C(OCC)(=O)C.[Os](=O)(=O)(=O)=O>[OH:31][CH:2]([CH2:3][OH:27])[CH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][N:8]([C:13]([O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:14])[CH2:7]2

Participants

7

Reactant 3

HCID 962Water2×HCID 82029Methyl morpholine oxideHCID 86725257HCID 86725257, compound

Product 1

HCID 86725258HCID 86725258, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of benzyl 5-allylisoindoline-2-carboxylate (294 mg, 1 mmol) in tert-butanol (2.5 mL) and water (2.5 mL) was added N-methylmorpholine-N-oxide (257 mg, 2.2 mmol) followed by osmium tetroxide solution (0.1 mL of 4% wt in water). The resulting mixture was stirred for 3 hr (during which time the mixture becomes homogeneous). This solution was diluted with ethyl acetate, washed with saturated sodium thiosulfate solution then brine, dried over magnesium sulfate and concentrated under vacuum. The residue was purified by silica chromatography (25 g silica eluted with 3-40% ethyl acetate in hexane) to give the title compound as a white solid.

Workup

  1. washwashed with saturated sodium thiosulfate solution
  2. dry with materialbrine, dried over magnesium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by silica chromatography (25 g silica eluted with 3-40% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-9a0fed1d0a974b60bb3ec7d65c374e34
Source dataset
uspto-grants-2015_05
Patent number
US09040504B2

Reaction notes

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