Dimethyl Sulfoxide → tert-butyl (5R)-1-oxaspiro[2.5]octan-5-ylcarbamate

HRID 530862Notes

Reaction equation

HRID 530862 reaction equation
[H-].[Na+].[O:3]=[C:4]1[CH2:9][CH2:8][CH2:7][CH:6]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:5]1.[CH3:18]S(C)=O>>[O:3]1[C:4]2([CH2:9][CH2:8][CH2:7][C@@H:6]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:16])[CH3:15])[CH2:5]2)[CH2:18]1

Participants

4

Reactant 3

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 44228975(3-Oxo-cyclohexyl)-carbamic acid tert-butyl ester

Product 1

HCID 86698241tert-butyl (5R)-1-oxaspiro[2.5]octan-5-ylcarbamate

Procedure

To a solution of Me3SOI (56.2 mmol) in DMSO (80 ml) was added NaH (51.5 mmol) and stirred at room temperature for 2 h until the solution become clear. The resulting solution was added tert-butyl 3-oxocyclohexylcarbamate (23.4 mmol) and stirred at rt overnight. The reaction was quenched with water and extracted with hexane. The extracts were combined and dried using anhydrous sodium sulfate. The product was purified using Biotage. The final products, isomer 1 and isomer 2, were well separated on silicon column with 15%-20% ethyl acetate in hexane. Each single diastereomer was used for the next step.

Workup

  1. stirringstirred at rt overnight
  2. customThe reaction was quenched with water
  3. extractionextracted with hexane
  4. customdried
  5. customThe product was purified
  6. customThe final products, isomer 1 and isomer 2, were well separated on silicon column with 15%-20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-9e2d1b2685c74d4189e29bf6c505545e
Source dataset
uspto-grants-2016_05
Patent number
US09351965B2

Reaction notes

Loading…