Methyl chloroformate → HCID 66936675, compound

HRID 1366715Notes

Reaction equation

HRID 1366715 reaction equation
C(=O)(O)[O-].[Na+].[NH2:6][C@H:7]1[CH2:11][CH2:10][N:9]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH2:8]1.[CH3:22][O:23][C:24](Cl)=[O:25]>O.C(Cl)Cl>[CH3:22][O:23][C:24]([NH:6][C@H:7]1[CH2:11][CH2:10][N:9]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH2:8]1)=[O:25]

Participants

6

Reactant 3

HCID 6586Methyl chloroformateHCID 516892Sodium BicarbonateHCID 1519355(S)-1-Cbz-3-Aminopyrrolidine

Product 1

HCID 66936675HCID 66936675, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium bicarbonate (2.073 g, 24.68 mmol) was dissolved in a mixture of water (20.00 mL) and DCM (20 mL), and phenylmethyl (3S)-3-amino-1-pyrrolidinecarboxylate (2.88 g, 11.22 mmol) was added followed by methylchloroformate (0.953 mL, 12.34 mmol). This mixture was stirred for 6 h. The biphasic mixture was then separated, and the aqueous phase was extracted once with DCM. The combined organics were dried over sodium sulfate, filtered and evaporated. The residual material was then purified via silica gel chromatography (0-100% EtoAc in hexane) yielding phenylmethyl (3S)-3-{[(methyloxy)carbonyl]amino}-1-pyrrolidinecarboxylate (2 g, 64%) as a clear oil. LCMS: (M+H)+: 278.9.

Workup

  1. additionwas added
  2. customThe biphasic mixture was then separated
  3. extractionthe aqueous phase was extracted once with DCM
  4. dry with materialThe combined organics were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residual material was then purified via silica gel chromatography (0-100% EtoAc in hexane)

Sources & evidence

ORD record
ord-73d6e09688f044588ed9a2a14160f027
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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