Triethylamine → HCID 13235317, compound

HRID 19730Notes

Reaction equation

HRID 19730 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][C@H:8]1[CH2:16][C:11]2([O:15][CH2:14][CH2:13][O:12]2)[CH2:10][C@H:9]1[CH2:17][OH:18].C(N(CC)CC)C>ClCCl>[CH3:1][S:2]([O:6][CH2:7][C@H:8]1[CH2:16][C:11]2([O:12][CH2:13][CH2:14][O:15]2)[CH2:10][C@H:9]1[CH2:17][O:18][S:2]([CH3:1])(=[O:4])=[O:3])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 13235313HCID 13235313, compound

Product 1

HCID 13235317HCID 13235317, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Methanesulfonyl chloride (1.93 ml, 24.9 mmol) is added to a cooled (0° C.) solution of ((7R,8S)-8-hydroxymethyl-1,4-dioxa-spiro[4.4]non-7-yl)-methanol (Tet. Lett., 2002,43, 4947; 1.17 g, 6.22 mmol) and triethylamine (3.50 ml, 24.9 mmol) in dichloromethane (30 ml). The reaction is stirred for 2 hours at 0° C. and then partitioned between dichloromethane and iced water. The organic phase is washed with 1M aqueous HCl, saturated aqueous NaHCO3, brine, dried (MgSO4) and evaporated to afford methanesulfonic acid (7R,8S)-8-methane-sulfonyloxymethyl-1,4-dioxaspiro[4.4]non-7-ylmethyl ester, MH+345.

Workup

  1. custompartitioned between dichloromethane and iced water
  2. washThe organic phase is washed with 1M aqueous HCl, saturated aqueous NaHCO3, brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-f2c4ffab454f4e5fb01a4d05bb21455e
Source dataset
uspto-grants-2010_06
Patent number
US07745462B2

Reaction notes

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