4-Toluenesulfonyl chloride → HCID 58551088, compound

HRID 1908033Notes

Reaction equation

HRID 1908033 reaction equation
[OH:1]/[N:2]=[C:3]1\[CH2:4][C:5]2([O:18][C:19]3[C:24]\1=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2.[CH3:25][C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1>N1C=CC=CC=1>[S:32]([O:1]/[N:2]=[C:3]1\[CH2:4][C:5]2([O:18][C:19]3[C:24]\1=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)([C:29]1[CH:30]=[CH:31][C:26]([CH3:25])=[CH:27][CH:28]=1)(=[O:34])=[O:33]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 58551619tert-Butyl (4E)-4-(hydroxyimino)-3,4-dihydro-1'H-spiro[1-benzopyran-2,4'-piperidine]-1'-carboxylate

Product 1

HCID 58551088HCID 58551088, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of tert-butyl (4E)-4-hydroxyiminospiro[chromane-2,4′-piperidine]-1′-carboxylate (448 mg, 1.34 mmol) and 4-methylbenzenesulfonyl chloride (514 mg, 2.70 mmol) were stirred in pyridine (2.1 mL) at 0° C. for 6 hours. The reaction mixture was poured over ice and the mixture was extracted with ethyl acetate. The organics were dried over sodium sulfate and evaporated to give (E)-tert-butyl 4-(tosyloxyimino)spiro[chroman-2,4′-piperidine]-1′-carboxylate (532 mg, 81%). ESI-MS m/z calc. 486.2. found 487.5 (M+1)+; Retention time: 2.20 minutes (3 min run).

Workup

  1. additionThe reaction mixture was poured over ice
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organics were dried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-55dacebb4f39478598c07149664cef6b
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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