Methanol → N-tert-butoxycarbonyl-5-oxo-4-thiapiperidine

HRID 1676259Notes

Reaction equation

HRID 1676259 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1.C[OH:15]>O>[C:10]([O:9][C:7]([N:1]1[CH2:2][C:3](=[O:15])[S:4][CH2:5][CH2:6]1)=[O:8])([CH3:13])([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 887MethanolHCID 21949316Thiomorpholine, N-BOC protected

Product 1

HCID 67347522N-tert-butoxycarbonyl-5-oxo-4-thiapiperidineYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A mechanically-stirred mixture of tert-butyl thiomorpholine-4-carboxylate (243 g, 1.19 mol), MeOH (1.5 L), and H2O (1.5 L) was cooled to 0° C. Solid NaIO4 (280 g, 1.3 mol) was added in portions over a 2 hour period. For convenience, the suspension was stirred for 3 days at room temperature. The solids were filtered, washing with MeOH (3×500 mL). The filtrate was concentrated. Residual water was saturated with solid NaCl, and the aqueous phase was extracted with EtOAc (4×200 mL). The combined organic phases were dried (MgSO4), filtered, and concentrated to obtain the product (255 g, 97%).

Workup

  1. filtrationThe solids were filtered
  2. washwashing with MeOH (3×500 mL)
  3. concentrationThe filtrate was concentrated
  4. extractionthe aqueous phase was extracted with EtOAc (4×200 mL)
  5. dry with materialThe combined organic phases were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-40b3be5885594677ad86d2aec0f85ec0
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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