Triethylamine → HCID 118383050, compound

HRID 2202706Notes

Reaction equation

HRID 2202706 reaction equation
[CH:1]([CH:4]1[CH2:8][NH:7][C@@H:6]([CH2:9][OH:10])[CH2:5]1)([CH3:3])[CH3:2].C(N(CC)CC)C.[S:18](Cl)(Cl)(=[O:20])=[O:19]>C(Cl)Cl>[CH:1]([CH:4]1[CH2:8][N:7]2[S:18](=[O:20])(=[O:19])[O:10][CH2:9][C@H:6]2[CH2:5]1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24648Sulfuryl chlorideHCID 118383118HCID 118383118, compound

Product 1

HCID 118383050HCID 118383050, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of ((2R)-4-isopropylpyrrolidin-2-yl)methanol (1.639 g, 11.44 mmol) and triethylamine (3.18 mL, 22.89 mmol) in DCM (100 mL) was cooled to −78° C. To this mixture was added sulfuryl chloride, 1.0 M solution in DCM (13.73 mL, 13.73 mmol) dropwise. The reaction mixture was allowed to warm to room temperature overnight. The reaction mixture was concentrated onto a plug of silica gel and purified by ISCO, chromatograph through a REDISEP™ pre-packed silica gel column (40 g), eluting with a gradient of 0% to 10% MeOH (with 2 M NH3) in DCM to give (3aR)-5-isopropyltetrahydro-3H-pyrrolo[1,2-c][1,2,3]oxathiazole 1,1-dioxide (211.9 mg, 1.032 mmol, 9% yield) as light yellow oil. m/z (ESI, +ve) 206 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated onto a plug of silica gel
  2. custompurified by ISCO, chromatograph through a REDISEP™ pre-packed silica gel column (40 g)
  3. washeluting with a gradient of 0% to 10% MeOH (with 2 M NH3) in DCM

Sources & evidence

ORD record
ord-2c36b517530a4354aa453fcb71c68d7f
Source dataset
uspto-grants-2016_06
Patent number
US09365522B2

Reaction notes

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