Water → HCID 178505327, compound

HRID 1159406Notes

Reaction equation

HRID 1159406 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[N:6]1([CH2:12][C@@H:13]2[CH2:16][C@H:15]([OH:17])[CH2:14]2)[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1.C(N(CC)CC)C.O>C(Cl)Cl>[CH3:1][S:2]([O:17][C@H:15]1[CH2:16][C@@H:13]([CH2:12][N:6]2[CH2:11][CH2:10][O:9][CH2:8][CH2:7]2)[CH2:14]1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178521631HCID 178521631, compound

Product 1

HCID 178505327HCID 178505327, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

MsCl (0.27 mL, 3.5 mmol) was added dropwise to a solution of intermediate 40, cis-3-(Morpholin-4-ylmethyl)cyclobutanol (0.5 g, 2.9 mmol) and triethylamine (1 mL, 7.0 mmol) in CH2Cl2 (5 mL) in argon under stirring on an ice bath. The mixture was brought to room temperature for 1 h, water (10 mL) was added, and the layers were separated. The organic layer was washed with water. The water layer was washed with the saturated NaCl solution, dried over Na2SO4, and evaporated to give the title compound as a yellow oil in 99% (718 mg, 2.88 mmol) yield. This material was used without additional purification. 1H-NMR (400 MHz)-data (dmso-d6): 4.83 (dddd, 1H, J=7.5 Hz, CHOMs), 3.51-3.58 (m, 4H, CH2OCH2), 3.12 (s, 1H, Ms), 2.46-2.55 (m, 2H, cyclobutylCHH), 2.28-2.40 (m, 6H, (CH2)3N), 2.00-2.12 (m, 1H, CHCH2N), 1.80-1.89 (m, 2H, cyclobutylCHH).

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with water
  3. washThe water layer was washed with the saturated NaCl solution
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-d6131d6ae2f348a4b4d58bcbb59ab842
Source dataset
uspto-grants-2010_10
Patent number
US07812040B2

Reaction notes

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