Acetone → Tert-butyl 8-tert-butyl-10-(1,2-dihydroxyethyl)-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate

HRID 72914Notes

Reaction equation

HRID 72914 reaction equation
[C:1]([N:5]1[CH2:10][C:9]2([CH2:15][CH2:14][N:13]([C:16](OC(C)(C)C)=[O:17])[CH2:12][CH2:11]2)[O:8][CH:7]([CH:23]=C)[CH2:6]1)([CH3:4])([CH3:3])[CH3:2].C[N+]1([O-])CC[O:29][CH2:28]C1.[CH3:33][C:34]([OH:37])([CH3:36])[CH3:35].CC(C)=[O:40]>O.[Os](=O)(=O)(=O)=O>[C:1]([N:5]1[CH2:6][CH:7]([CH:23]([OH:40])[CH2:28][OH:29])[O:8][C:9]2([CH2:11][CH2:12][N:13]([C:16]([O:37][C:34]([CH3:36])([CH3:35])[CH3:33])=[O:17])[CH2:14][CH2:15]2)[CH2:10]1)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 180AcetoneHCID 6386tert-ButanolHCID 82029Methyl morpholine oxideHCID 68291485HCID 68291485, compound

Product 1

HCID 68291705Tert-butyl 8-tert-butyl-10-(1,2-dihydroxyethyl)-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Procedure

To tert-butyl 4-tert-butyl-2-vinyl-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate (1.00 g, 2.95 mmol) and 4-methylmorpholine 4-oxide (381 mg, 3.25 mmol) in acetone (9.0 mL) and water (1.0 mL) was added a solution of osmium tetroxide in 2-methyl-2-propanol (370 μL of 2.5% w/w, 0.0295 mmol) and the solution stirred 2 h. The reaction quenched with 300 mL of 1 M sodium bisulfate and stirred for 5 min. The mixture was extracted with ethyl acetate (2×200 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to provide tert-butyl 8-tert-butyl-10-(1,2-dihydroxyethyl)-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate as a white foamy solid. The crude material was taken directly to the next step. ESI-MS m/z calc. 372.3. Found 373.3 (M+1)+; Retention time: 0.83 minutes (3 min run).

Workup

  1. customThe reaction quenched with 300 mL of 1 M sodium bisulfate
  2. stirringstirred for 5 min
  3. extractionThe mixture was extracted with ethyl acetate (2×200 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c227572995324bf9b2b18e3e3abe2b8d
Source dataset
uspto-grants-2014_09
Patent number
US08828996B2

Reaction notes

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