1-tert-Butyl 2-methyl (2S)-4-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)pyrrolidine-1,2-dicarboxylate → Methyl 4-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-L-prolinate

HRID 2233945Notes

Reaction equation

HRID 2233945 reaction equation
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][CH:12]1[CH2:17][CH2:16][N:15]([CH:18]2[CH2:22][N:21](C(OC(C)(C)C)=O)[C@H:20]([C:30]([O:32][CH3:33])=[O:31])[CH2:19]2)[CH2:14][CH2:13]1)=[O:10]>Cl.O1CCOCC1>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][CH:12]1[CH2:13][CH2:14][N:15]([CH:18]2[CH2:22][NH:21][C@H:20]([C:30]([O:32][CH3:33])=[O:31])[CH2:19]2)[CH2:16][CH2:17]1)=[O:10]

Participants

4

Reactant 1

HCID 866082951-tert-Butyl 2-methyl (2S)-4-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)pyrrolidine-1,2-dicarboxylate

Product 1

HCID 68579931Methyl 4-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-L-prolinateYield 101.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

1-tert-Butyl 2-methyl (2S)-4-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)pyrrolidine-1,2-dicarboxylate (Example 51, 0.16 g, 0.32 mM) was stirred in 4 N hydrogen chloride in dioxane (4.0 ml) at room temperature for twenty minutes. The orange mixture was concentrated then dissolved in a small amount of MeOH/DCM, diluted with DCM, and washed with sodium bicarbonate. The organic layer was dried over MgSO4, filtered and concentrated to give an orange solid (0.130 g).

Workup

  1. concentrationThe orange mixture was concentrated
  2. dissolutionthen dissolved in a small amount of MeOH/DCM
  3. additiondiluted with DCM
  4. washwashed with sodium bicarbonate
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-043638ce1e214320b6f47d2bcfa07f63
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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