(S)-(+)-2-(Methoxymethyl)pyrrolidine → HCID 11668424, compound

HRID 853855Notes

Reaction equation

HRID 853855 reaction equation
[Cl:1][C:2]1[C:3]([S:16](Cl)(=[O:18])=[O:17])=[CH:4][C:5]2[C:6](=[O:15])[C:7]3[N:8]([CH2:11][CH2:12][CH2:13][N:14]=3)[C:9]=2[CH:10]=1.[CH3:20][O:21][CH2:22][C@@H:23]1[CH2:27][CH2:26][CH2:25][NH:24]1>C(Cl)Cl>[Cl:1][C:2]1[C:3]([S:16]([N:24]2[CH2:25][CH2:26][CH2:27][C@H:23]2[CH2:22][O:21][CH3:20])(=[O:18])=[O:17])=[CH:4][C:5]2[C:6](=[O:15])[C:7]3[N:8]([CH2:11][CH2:12][CH2:13][N:14]=3)[C:9]=2[CH:10]=1

Participants

4

Reactant 2

HCID 671217(S)-(+)-2-(Methoxymethyl)pyrrolidineHCID 58932540HCID 58932540, compound

Product 1

HCID 11668424HCID 11668424, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-chloro-10-oxo-2,3,4,10-tetrahydropyrimido[1,2-a]indole-8-sulfonyl chloride (0.140 g, 0.439 mmol) in CH2Cl2 (10 mL) was added (S)-(+)-2-(methoxymethyl)pyrrolidine (0.119 g, 0.965 mmol, 2.2 eq) drop-wise with cooling in an ice bath under a dry N2 atmosphere. After stirring at room temperature for 1.5 hr, the mixture was quenched with H2O (10 mL) and extracted with EtOAc (3×). The combined organic extracts were dried over MgSO4, filtered, and concentrated to give a film on glass. The film was combined with the product of an earlier run and purified on Biotage KP silica gel eluting with a step gradient of 20/80 petroleum ether/EtOAc, followed by 100% EtOAc to give the title compound as a bright yellow solid (0.104 g, 52.3% yield). Anal. Calc'd. for C17H20ClN3O4S.0.2H2O: C, 50.86; H, 5.12; N, 10.47. Found, C, 50.82; H, 5.00; N, 10.31. NMR (400 MHz, DMSO-d6): consistent. MS: (ES−) m/z 396/398 [M−H] 1 chlorine pattern observed. m.p.: 127-130° C. HRMS: consistent ESI Adduct [M+H] Exact 398.09358, Expt'l 398.09411, mmu 0.53, ppm 1.34, RI % 100.

Workup

  1. temperaturewith cooling in an ice bath under a dry N2 atmosphere
  2. customthe mixture was quenched with H2O (10 mL)
  3. extractionextracted with EtOAc (3×)
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a film on glass
  8. custompurified on Biotage KP silica gel eluting with a step gradient of 20/80 petroleum ether/EtOAc

Sources & evidence

ORD record
ord-5d286f0e8c9248dc825b434e92f31446
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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