3-t-Butyldiphenylsilyloxy-1-(4-hydroxymethyl-1,3-thiazol-2-yl)azetidine → 3-t-Butyldiphenylsilyloxy-1-(4-formyl-1,3-thiazol-2-yl)azetidine

HRID 891548Notes

Reaction equation

HRID 891548 reaction equation
[Si:1]([O:18][CH:19]1[CH2:22][N:21]([C:23]2[S:24][CH:25]=[C:26]([CH2:28][OH:29])[N:27]=2)[CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[Si:1]([O:18][CH:19]1[CH2:22][N:21]([C:23]2[S:24][CH:25]=[C:26]([CH:28]=[O:29])[N:27]=2)[CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 1

HCID 222428843-t-Butyldiphenylsilyloxy-1-(4-hydroxymethyl-1,3-thiazol-2-yl)azetidine

Product 1

HCID 222430493-t-Butyldiphenylsilyloxy-1-(4-formyl-1,3-thiazol-2-yl)azetidineYield 92%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-t-butyldiphenylsilyloxy-1-(4-hydroxymethyl-1,3-thiazol-2-yl)azetidine (3.88 g, 9.15 mmol) (obtained as described in Reference Example 2(2)) in anhydrous methylene chloride (194 ml) were added activated manganese dioxide (19.4 g) and the mixture was stirred at room temperature for 7 hours. After checking the completion of the reaction, the reaction mixture was filtered and the filtrate concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using n-hexane:ethyl acetate (3:1→1:1) as the eluant to afford 3-t-butyldiphenylsilyloxy-1-(4-formyl-1,3-thiazol-2-yl)azetidine (3.54 g, yield 92%) as a white solid.

Workup

  1. customthe completion of the reaction
  2. filtrationthe reaction mixture was filtered
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-cb7809c264294da6b3ba83ce7c81203f
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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