Nitrogen → HCID 57659775, compound

HRID 1011609Notes

Reaction equation

HRID 1011609 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH:20]1[CH2:22][CH2:21]1)[CH2:10][C:11](=[O:19])[C:12](=[N+]=[N-])[C:13]([O:15][CH3:16])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].N#N>C(Cl)Cl>[CH:20]1([C@H:9]2[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH:12]([C:13]([O:15][CH3:16])=[O:14])[C:11](=[O:19])[CH2:10]2)[CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 947NitrogenHCID 86629547HCID 86629547, compound

Product 1

HCID 57659775HCID 57659775, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-Methyl 5-(tert-butoxycarbonylamino)-5-cyclopropyl-2-diazo-3-oxopentanoate (30) (2.75 g, 8.84 mmol) was dissolved in CH2Cl2 (45 mL). The solution was evacuated and purged with N2 three times after which Rh2(OAc)4 (195 mg, 0.44 mmol) was added. The resulting green solution was stirred at rt for 1 h and was subsequently concentrated under vacuum. The residue was purified on a silica gel column (eluant hexane/EtOAc, 9/1 to 1/1 to give 1.75 g (70%) of (5S)-1-tert-butyl 2-methyl 5-cyclopropyl-3-oxopyrrolidine-1,2-dicarboxylate (31). Retention time (min)=1.981 method [1], MS (m/z) 306.2 (M+Na)+.

Workup

  1. customThe solution was evacuated
  2. additionwas added
  3. concentrationwas subsequently concentrated under vacuum
  4. customThe residue was purified on a silica gel column (eluant hexane/EtOAc, 9/1 to 1/1

Sources & evidence

ORD record
ord-e43b900400db46feaf5a9c6367cc8edc
Source dataset
uspto-grants-2011_07
Patent number
US07977368B2

Reaction notes

Loading…