Methanol → Tert-butyl (1-(3,4-dichlorophenylsulfonyl)pyrrolidin-2-yl)methylcarbamate

HRID 880019Notes

Reaction equation

HRID 880019 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9](Cl)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].[NH:13]1[CH2:17][CH2:16][CH2:15][CH:14]1[CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23].C(N(CC)CC)C.CO>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:13]2[CH2:17][CH2:16][CH2:15][CH:14]2[CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:24])([CH3:23])[CH3:25])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 887MethanolHCID 7383Benzenesulfonyl chloride, 3,4-dichloro-HCID 8471TriethylamineHCID 21834643Pyrrolidin-2-ylmethyl-carbamic acid tert-butyl ester

Product 1

HCID 86730078Tert-butyl (1-(3,4-dichlorophenylsulfonyl)pyrrolidin-2-yl)methylcarbamateYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3,4-dichlorobenzene-1-sulfonyl chloride (490 mg, 2.00 mmol) was added tert-butyl pyrrolidin-2-ylmethylcarbamate (400 mg, 2.00 mmol), followed by triethylamine (0.278 mL, 2.00 mmol). The reaction was stirred at rt overnight. The reaction mixture was diluted with DCM and washed with 1N HCl, H2O and brine, dried over Na2SO4 and decanted. The solvent was evaporated under reduced pressure and the crude product was purified on a 24 g silica gel cartridge using 0 to 100% EtOAc in hexane for 15 min, then 0 to 20% MeOH in DCM for 15 min to provide Intermediate 2A (800 mg, 1.95 mmol, 98% yield) as a white solid. HPLC/MS (Method D) RT=2.12 min, [M+1]+ 309.1.

Workup

  1. washwashed with 1N HCl, H2O and brine
  2. dry with materialdried over Na2SO4
  3. customdecanted
  4. customThe solvent was evaporated under reduced pressure
  5. customthe crude product was purified on a 24 g silica gel cartridge
  6. customfor 15 min

Sources & evidence

ORD record
ord-4611673fddb94d27bf6bb581fc4e0f46
Source dataset
uspto-grants-2015_03
Patent number
US08993557B2

Reaction notes

Loading…