Methanesulfonyl chloride → HCID 86695585, compound

HRID 1465719Notes

Reaction equation

HRID 1465719 reaction equation
[OH:1][CH:2]1[CH2:8][C@@H:7]2[N:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@@H:4]([CH2:5][CH2:6]2)[CH:3]1[C:17]([O:19][CH3:20])=[O:18].[CH3:21][S:22](Cl)(=[O:24])=[O:23].C(N(CC)C(C)C)(C)C>ClCCl>[CH3:21][S:22]([O:1][CH:2]1[CH2:8][C@@H:7]2[N:9]([C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[C@@H:4]([CH2:5][CH2:6]2)[CH:3]1[C:17]([O:19][CH3:20])=[O:18])(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 86695583HCID 86695583, compound

Product 1

HCID 86695585HCID 86695585, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(1S,5R)-8-Tert-butyl 2-methyl 3-hydroxy-8-azabicyclo[3.2.1]octane-2,8-dicarboxylate (1.75 g, 6.14 mmol) was dissolved in dichloromethane (30 mL), methanesulfonyl chloride (0.95 mL, 123 mmol) was added, followed by dropwise addition of N,N-diisopropylethyl-amine (5.29 mL, 30.7 mmol). The reaction mixture was stirred at room temperature overnight. After quench with saturated NaHCO3, the reaction mixture was extracted with dichloro-methane. The combined organic layer was washed with water and brine. Dried and concentrated to give 2.23 g of crude product. The crude was carried over the next step without further purification.

Workup

  1. customAfter quench with saturated NaHCO3
  2. extractionthe reaction mixture was extracted with dichloro-methane
  3. washThe combined organic layer was washed with water and brine
  4. customDried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-82fc964a2b5a4458949c27b5e47a6351
Source dataset
uspto-grants-2015_04
Patent number
US08999966B2

Reaction notes

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