Water → HCID 117603884, compound

HRID 1481966Notes

Reaction equation

HRID 1481966 reaction equation
[S:1](Cl)([CH3:4])(=[O:3])=[O:2].[CH2:6]([C:10]1([CH2:23][OH:24])[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1)[CH2:7][CH:8]=[CH2:9].O>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:6]([C:10]1([CH2:23][O:24][S:1]([CH3:4])(=[O:3])=[O:2])[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])[CH2:14][CH2:15]1)[CH2:7][CH:8]=[CH2:9]

Participants

6

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 117603750HCID 117603750, compound

Product 1

HCID 117603884HCID 117603884, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Ms-Cl (5.59 mL, 71.7 mmol) was added dropwise at 0° C. to a stirred solution of tert-butyl 4-(but-3-en-1-yl)-4-(hydroxymethyl)piperidine-1-carboxylate (16.1 g, 59.8 mmol) TEA (16.66 mL, 120 mmol) and DMAP (0.365 g, 2.99 mmol) in CH2Cl2 (300 mL) and the mixture was stirred at room temp for 2 h. Water was then added and the mixture was extracted with methylene chloride (100 mL), dried (Na2SO4), filtered and concentrated. The residue was purified by Biotage (0-40% Hex/EtOAc) to afford tert-butyl 4-(but-3-en-1-yl)-4-(((methylsulfonyl)oxy)methyl)piperidine-1-carboxylate (18 g, 51.8 mmol, 87% yield) as colorless oil. 1H NMR (500 MHz, CDCl3) δ 5.88-5.75 (m, 1H), 5.11-4.90 (m, 2H), 4.09 (s, 2H), 3.58-3.44 (m, 2H), 3.40-3.32 (m, 2H), 3.05 (s, 3H), 2.07-2.02 (m, 2H), 1.59-1.54 (m, 2H), 1.53-1.49 (m, 4H), 1.48 (s, 9H).

Workup

  1. extractionthe mixture was extracted with methylene chloride (100 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by Biotage (0-40% Hex/EtOAc)

Sources & evidence

ORD record
ord-662db902669c498185c1bb248df033fd
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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