4-Toluenesulfonyl chloride → HCID 69148474, compound

HRID 747019Notes

Reaction equation

HRID 747019 reaction equation
[OH:1][CH:2]([C:7]1([CH2:23]O)[CH2:12][CH2:11][N:10]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:9][CH2:8]1)[C:3]([OH:6])([CH3:5])[CH3:4].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.C(N(CC)CC)C>ClCCl>[OH:1][CH:2]1[C:7]2([CH2:8][CH2:9][N:10]([C:13]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[O:14])[CH2:11][CH2:12]2)[CH2:23][O:6][C:3]1([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471Triethylamine2×HCID 69147839HCID 69147839, compound

Product 1

HCID 69148474HCID 69148474, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyl 4-(1,2-dihydroxy-2-methylpropyl)-4-(hydroxymethyl)piperidine-1-carboxylate (from step (iii) above; 340 mg) was dissolved in dichloromethane and p-toluenesulfonyl chloride (190 mg) was added, followed by triethylamine (0.14 mL). This mixture was stirred for 2 h and a second aliquot of triethylamine was added and the mixture was stirred for 12 h. The mixture was concentrated in vacuo. The crude product was purified by chromatography on silica using 50-100% ethyl acetate in iso-hexane as eluant to afford the product (190 mg).

Workup

  1. stirringthe mixture was stirred for 12 h
  2. concentrationThe mixture was concentrated in vacuo
  3. customThe crude product was purified by chromatography on silica using 50-100% ethyl acetate in iso-hexane as eluant

Sources & evidence

ORD record
ord-83af963832be476d8e6427cd389361f0
Source dataset
uspto-grants-2008_07
Patent number
US07393858B2

Reaction notes

Loading…