Triethylamine → HCID 86645838, compound

HRID 1253728Notes

Reaction equation

HRID 1253728 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH:7]1[CH2:24][CH2:23][C:10]2([CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)[CH2:9][CH2:8]1.CCN(CC)CC>>[CH3:1][S:2]([O:6][CH:7]1[CH2:8][CH2:9][C:10]2([CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:12][CH2:11]2)[CH2:23][CH2:24]1)(=[O:4])=[O:3]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66701044tert-Butyl 9-hydroxy-3-azaspiro[5.5]undecane-3-carboxylate

Product 1

HCID 86645838HCID 86645838, compoundYield 88%

Procedure

Methanesulfonyl chloride (0.98 ml, 12.27 mmol, 1.5 eq.) was added to a solution of tert-butyl 9-hydroxy-3-azaspiro[5.5]undecane-3-carboxylate (2.20 g, 8.18 mmol, 1.0 eq.) (see step-6 product of AMN-38) and Et3N (2.84 ml, 20.45 mmol, 2.5 eq.) in MC (20 ml) at 0° C. and the resulting reaction mixture was stirred at RT for 14 h. The reaction mixture was diluted with MC (50 ml) and washed with sat. NH4Cl solution (2×25 ml) and brine (2×25 ml) and then dried over sodium sulfate. The solvent was removed under reduced pressure and the crude product was purified by column chromatography (silica gel; 10% ethyl acetate/hexanes) to give the desired compound as a light orange solid. Yield: 88% (2.84 g, 8.18 mmol).

Workup

  1. customat 0° C.
  2. customthe resulting reaction mixture
  3. additionThe reaction mixture was diluted with MC (50 ml)
  4. washwashed with sat. NH4Cl solution (2×25 ml) and brine (2×25 ml)
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe crude product was purified by column chromatography (silica gel; 10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-52f6467802d34ce68c3466acb1f05d32
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

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