Water → HCID 67486290, compound

HRID 1881045Notes

Reaction equation

HRID 1881045 reaction equation
[C:1]([O:5][C:6](=[O:18])[N:7]([CH2:15][CH2:16][OH:17])[C@H:8]1[CH2:13][CH2:12][C@H:11]([CH3:14])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[Cl:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22]Br.[H-].[Na+].O>CN(C=O)C>[C:1]([O:5][C:6](=[O:18])[N:7]([CH2:15][CH2:16][O:17][CH2:22][C:21]1[CH:24]=[CH:25][CH:26]=[CH:27][C:20]=1[Cl:19])[CH:8]1[CH2:9][CH2:10][CH:11]([CH3:14])[CH2:12][CH2:13]1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 11905alpha-Bromo-o-chlorotolueneHCID 24758Sodium hydrideHCID 178453761HCID 178453761, compound

Product 1

HCID 67486290HCID 67486290, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of (2-hydroxy-ethyl)-(trans-4-methyl-cyclohexyl)-carbamic acid tert-butyl ester (0.75 g, 2.91 mmol) and 2-chlorobenzylbromide (0.90, 4.37 mmol) in DMF (8 mL) was added NaH (60% in mineral oil, 0.23 g, 5.83 mmol) and the reaction mixture was stirred for 16 h. H2O (4 mL) was added and the mixture was extracted with diethyl ether (3×5 mL). The organic phase was collected and the solvent was removed in vacuo to give the crude product of [2-(2-chloro-benzyloxy)-ethyl]-(4-methyl-cyclohexyl)-carbamic acid tert-butyl ester. This was dissolved in DCM (4 mL) and TFA (4 mL) was added and the mixture was stirred for 2 hs before the volatiles were removed in vacuo.

Workup

  1. extractionthe mixture was extracted with diethyl ether (3×5 mL)
  2. customThe organic phase was collected
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-db798ea7491943b6a49f066a9fac5130
Source dataset
uspto-grants-2012_11
Patent number
US08318778B2

Reaction notes

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