2-Methyltetrahydrofuran → N-cyclohexylmethyl-(2-oxoethyl)-carbamic acid benzyl ester

HRID 1500627Notes

Reaction equation

HRID 1500627 reaction equation
S(=O)(=O)(O)O.[CH2:6]([O:13][C:14](=[O:26])[N:15]([CH2:23][CH:24]=[O:25])[CH2:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CC1OCCC1.[OH-].[Na+]>O>[CH2:6]([O:13][C:14](=[O:26])[N:15]([CH2:23][CH:24]=[O:25])[CH2:16][CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 73012-MethyltetrahydrofuranHCID 14798Sodium HydroxideHCID 117775085N-cyclohexylmethyl-(2-oxoethyl)-carbamic acid benzyl ester bisulfate

Product 1

HCID 25006349N-cyclohexylmethyl-(2-oxoethyl)-carbamic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 100 mL flask was added N-cyclohexylmethyl-(2-oxoethyl)-carbamic acid benzyl ester bisulfate adduct (3.94 g, 1 mmol) and MeTHF (35 mL), followed by water (25 mL). The resulting slurry was stirred at room temperature for 5 min and 1 M NaOH (8 mL) was added. The reaction mixture was stirred at room temperature for 45 min. The layers were separated and the volume of the organic layer was reduced to ˜8 mL to provide the crude title intermediate.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 45 min
  2. customThe layers were separated

Sources & evidence

ORD record
ord-1d5e6a390bd64cd399b4d87fd44f2ae4
Source dataset
uspto-grants-2015_12
Patent number
US09206172B2

Reaction notes

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