Pyridine → Ammonia

HRID 255137Notes

Reaction equation

HRID 255137 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1.[N:20]1C=CC=CC=1>C(Cl)Cl>[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][O:8][S:15]([C:12]2[CH:13]=[CH:14][C:9]([CH3:19])=[CH:10][CH:11]=2)(=[O:17])=[O:16])[CH2:3][CH2:2]1.[NH3:20]

Participants

6

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 2773573(Oxan-4-yl)methanol

Product 2

HCID 222AmmoniaHCID 19077576(Tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tetrahydro-2-H-pyran-4-ylmethanol (Combi-Blocks, 2.0 g, 17 mmol) and p-toluenesulfonyl chloride (3.5 g, 18 mmol) in 10 mL of CH2Cl2 and 10 mL of pyridine were processed as in Example 160A to afford the title compound MS (DCI/NH3) m/z 288 (M+NH4)+.

Sources & evidence

ORD record
ord-d6ca42b7fec541348251a8af37b075b0
Source dataset
uspto-grants-2011_01
Patent number
US07875639B2

Reaction notes

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