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

HRID 1423298Notes

Reaction equation

HRID 1423298 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 1M 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-aaa423c181d24fd884e151bd37103a77
Source dataset
uspto-grants-2015_01
Patent number
US08927573B2

Reaction notes

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