Sodium Sulfite → 3-(1-(Tert-butyldimethylsilyloxy)cyclobutyl)propane-1,2-diol

HRID 1696322

Reaction equation

HRID 1696322 reaction equation
[CH2:1]([C:4]1([O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])[CH2:7][CH2:6][CH2:5]1)C=C.O.CC([OH:21])(C)C.C[N+]1([O-])[CH2:28][CH2:27][O:26]CC1.S([O-])([O-])=O.[Na+].[Na+]>[Os](=O)(=O)(=O)=O.O>[Si:9]([O:8][C:4]1([CH2:1][CH:27]([OH:26])[CH2:28][OH:21])[CH2:7][CH2:6][CH2:5]1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]

Participants

7

Reactant 4

HCID 24437Sodium SulfiteHCID 82029Methyl morpholine oxideHCID 66844818(1-Allylcyclobutoxy)(tert-butyl)dimethylsilaneHCID 714019492-Methylpropan-2-ol--water (1/1)

Product 1

HCID 668451483-(1-(Tert-butyldimethylsilyloxy)cyclobutyl)propane-1,2-diol

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Procedure

To a 2 L round bottomed flask was added (1-allylcyclobutoxy) (tert-butyl)dimethylsilane (previous step) and H2O/t-BuOH (1:1, 1 L). NMO (32.68 g, 279 mmol) was added to the mixture. After stirring for 5 min the solution was found to be homogenous. Osmium tetroxide (1.00 g, 3.93 mmol) was added and the reaction was stirred at RT. After 2 h, TLC revealed the reaction to be complete. 500 mL of H2O and sodium sulfite (19.5 g, 155 mmol) were added and the reaction was stirred for another hour. The aqueous solution was extracted with ether (2×1 L). The combined organics were concentrated in vacuo to give 3-(1-(tert-butyldimethylsilyloxy)cyclobutyl)propane-1,2-diol, as a light yellow oil. The oil contained some t-BuOH, but was carried forward without further purification.

Workup

  1. stirringthe reaction was stirred at RT
  2. waitAfter 2 h
  3. customthe reaction
  4. stirringthe reaction was stirred for another hour
  5. extractionThe aqueous solution was extracted with ether (2×1 L)
  6. concentrationThe combined organics were concentrated in vacuo

Sources & evidence

ORD record
ord-7dbd3081f1424549a5625553e636acc7
Source dataset
uspto-grants-2012_04
Patent number
US08163766B2

Linked notes

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