Formic Acid → 1-(Tert-butyl) 3-methyl 3-formamidopyrrolidine-1,3-dicarboxylate

HRID 1038095Notes

Reaction equation

HRID 1038095 reaction equation
[CH:1](O)=[O:2].[CH3:4][O:5][C:6]([C:8]1([NH2:20])[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9]1)=[O:7].ClC1N=C(OC)N=C(OC)N=1.CN1CCOCC1>CN(C1C=CN=CC=1)C>[CH3:4][O:5][C:6]([C:8]1([NH:20][CH:1]=[O:2])[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])[CH2:9]1)=[O:7]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 79724-MethylmorpholineHCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 576862811-Tert-butyl 3-methyl 3-aminopyrrolidine-1,3-dicarboxylate

Product 1

HCID 576860951-(Tert-butyl) 3-methyl 3-formamidopyrrolidine-1,3-dicarboxylate

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

Added formic acid (200 mg, 4.34 mmol) to solution of 3-Amino-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (1T) (900 mg, 3.688 mmol); 2-Chloro-4,6 dimethoxy-1,3,5-Triazine (CDMT) (800 mg, 4.556 mmol); DMAP (20 mg), and NMM (400 mg, 4 mmol) at room temperature, then stirred overnight. The solvent was evaporated and the residue extracted with MeCl2 (200 ml), washed with H2O (50 ml), dried over MgSO4, filtered and solvent evaporated yielding a solid which chromatographed on silica gel eluting with 5% MeOH/MeCl2 containing 2% NH4OH yielding 2T as a white solid (725 mg, 72%) LCMS (MH 273) Retention time=2.53 minutes.

Workup

  1. customThe solvent was evaporated
  2. extractionthe residue extracted with MeCl2 (200 ml)
  3. washwashed with H2O (50 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customsolvent evaporated
  7. customyielding a solid which
  8. customchromatographed on silica gel eluting with 5% MeOH/MeCl2 containing 2% NH4OH yielding 2T as a white solid (725 mg, 72%) LCMS (MH 273) Retention time=2.53 minutes

Sources & evidence

ORD record
ord-8a581bbb284949beaed372b5c7576a7d
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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