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

HRID 43255

Reaction equation

HRID 43255 reaction equation
S(=O)(O)O.[CH2:5]([O:12][C:13](=[O:25])[N:14]([CH2:22][CH:23]=[O:24])[CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CC1OCCC1.[OH-].[Na+]>O>[CH2:5]([O:12][C:13](=[O:25])[N:14]([CH2:22][CH:23]=[O:24])[CH2:15][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 73012-MethyltetrahydrofuranHCID 14798Sodium HydroxideHCID 86615227N-cyclohexylmethyl-(2-oxoethyl)-carbamic acid benzyl ester bisulfite

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 bisulfite 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-e39f06a0806346ccbd6359700447595b
Source dataset
uspto-grants-2013_09
Patent number
US08536335B2

Linked notes

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