Dichloromethane → HCID 118383643, compound

HRID 2202762Notes

Reaction equation

HRID 2202762 reaction equation
[C:1]([N:8]1[CH2:12][C@H:11]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:10][C@H:9]1[C:19](O)=[O:20])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(Cl)Cl.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[CH3:38][NH:39][O:40][CH3:41]>CCOC(C)=O>[CH:13]1([C@H:11]2[CH2:12][N:8]([C:1]([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2])[C@H:9]([C:19](=[O:20])[N:39]([O:40][CH3:41])[CH3:38])[CH2:10]2)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 682631,1'-CarbonyldiimidazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 2756008(2S,4S)-Boc-4-cyclohexyl-pyrrolidine-2-carboxylic acid

Product 1

HCID 118383643HCID 118383643, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(2S,4S)-Boc-4-cyclohexyl-pyrrolidine-2-carboxylic acid (Chem Impex Int'l, Wood Dale, Ill., 997 mg, 3.35 mmol) was treated with DCM (25 mL) followed by 1,1′-carbonyldiimidazole (598 mg, 3.69 mmol). The solution was allowed to stir at room temperature for 1.5 h then the reaction mixture was then treated with N,O-dimethyl hydroxylamine hydrochloride (360 mg, 3.69 mmol) and allowed to stir over the weekend at room temperature. The reaction mixture was diluted with EtOAc (50 mL), washed with a saturated solution of NaHCO3 (30 mL) and brine (30 mL), dried over MgSO4, filtered and concentrated affording crude (2S,4S)-tert-butyl 4-cyclohexyl-2-(methoxy(methyl)carbamoyl)pyrrolidine-1-carboxylate (1.14 g, 3.35 mmol, 99% yield) as a clear, colorless viscous oil. MS (ESI) 363.2 [M+Na]+. The crude material was used in the next step without further purification.

Workup

  1. stirringto stir over the weekend at room temperature
  2. washwashed with a saturated solution of NaHCO3 (30 mL) and brine (30 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-27c87356b5884c94be5e2f71668c041e
Source dataset
uspto-grants-2016_06
Patent number
US09365522B2

Reaction notes

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