Methanesulfonyl chloride → tert-butyl 5-[(methylsulfonyl)oxy]hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate

HRID 1804607Notes

Reaction equation

HRID 1804607 reaction equation
[OH:1][CH:2]1[CH2:16][CH:5]2[CH2:6][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][CH:4]2[CH2:3]1.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:17][S:18]([O:1][CH:2]1[CH2:16][CH:5]2[CH2:6][N:7]([C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])[CH2:8][CH:4]2[CH2:3]1)(=[O:20])=[O:19]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 22594656tert-Butyl 5-hydroxyhexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate

Product 1

HCID 21076290tert-butyl 5-[(methylsulfonyl)oxy]hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylateYield 75%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of the title compound from Step A above (550 mg, 2.4 mmol) and DMAP (296 mg) in DCM (15 mL) was added MsCl (189 μL) at 0° C. The mixture was stirred for 10 min at the same temperature and for an additional hour at RT. The mixture was quenched with ice water and extracted with ethyl acetate (2×50 mL). The organic layer was washed with water and brine, dried over sodium sulfate, filtered, and concentrated under vacuum. The residue oil was purified via prep-plate purification eluting with 50% ethyl acetate in hexane to afford the title compound (i-39) (555 mg, 75%). ESI-MS calculated for C13H23NO5S: Exact Mass: 305.13. Found 328.14 (MNa)+.

Workup

  1. customThe mixture was quenched with ice water
  2. extractionextracted with ethyl acetate (2×50 mL)
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue oil was purified via prep-plate purification
  8. washeluting with 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-ce0e19c8e6df462884bc4bf6cd207bf7
Source dataset
uspto-grants-2013_01
Patent number
US08354403B2

Reaction notes

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