N-Carbethoxyphthalimide → HCID 56635400, compound

HRID 1740478Notes

Reaction equation

HRID 1740478 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([NH2:13])[CH2:10][C@@H:9]1[CH2:14][OH:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(N1[C:25](=[O:26])[C:24]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]2[C:22]1=[O:31])=O)C>CO>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([N:13]2[C:25](=[O:26])[C:24]3=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]3[C:22]2=[O:31])[CH2:10][C@@H:9]1[CH2:14][OH:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 31187N-CarbethoxyphthalimideHCID 44828601tert-Butyl (2R,4S)-4-amino-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Product 1

HCID 56635400HCID 56635400, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(2R,4S)-1-(tert-Butyloxycarbonyl)-2-hydroxymethyl-4-amino-pyrrolidine 41 (1.00 g, 4.63 mmol) was dissolved in dry methanol (20 ml) and treated with N-ethoxycarbonyl phthalimide (1.09 g, 5 mmol) at room temperature. The reaction mixture was stirred for 6 h and evaporated to dryness the residue was purified by flash chromatography over silica gel using CH2Cl2 →EtOAc as the eluent. The pure fractions were collected and evaporated to give 1.5 g (94%) of pure compound as foam. 1HNMR (CDCl3): 1.45 (s, 9H, Boc), 1.90 (dd, 1H), 2.34 (m, 1H), 3.40-3.62 (m, 3H), 4.00 (m, 2H), 4.28 (bs, 1H), 4.44 (m, 1H) and 7.3-7.6 (m, 4H, Ph).

Workup

  1. customevaporated to dryness the residue
  2. customwas purified by flash chromatography over silica gel
  3. customThe pure fractions were collected
  4. customevaporated

Sources & evidence

ORD record
ord-e94787686841466f9e8e0776d413fe3c
Source dataset
uspto-grants-1999_10
Patent number
US05969135

Reaction notes

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