4-Toluenesulfonyl chloride → HCID 58551088, compound

HRID 2204118Notes

Reaction equation

HRID 2204118 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-dadb9040a5b14952a395eaddda544604
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

Loading…