Dichloromethane → HCID 131733576, compound

HRID 1749390Notes

Reaction equation

HRID 1749390 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH:5]([OH:8])[C:4]([CH3:10])([CH3:9])[CH2:3]1.C(=O)([O-])[O-].[Na+].[Na+].Cl[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19].ClCCl>C1COCC1.CO>[OH:8][CH:5]1[CH2:6][CH2:7][CH:2]([NH:1][C:18](=[O:19])[O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:3][C:4]1([CH3:10])[CH3:9]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 21291621HCID 21291621, compound

Product 1

HCID 131733576HCID 131733576, compoundYield 49.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-amino-2,2-dimethylcyclohexanol (1.0 equiv.) in 1.7 M sodium carbonate solution (1.3 equiv.) and THF (1.3 M) was added benzyl chloroformate (1.5 equiv.) slowly at 0° C. After addition, the mixture was stirred at room temperature overnight. TLC (dichloromethane:MeOH=10:1) showed that the reaction was completed. The mixture was filtered and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under vacuum to give crude racemic product, which was purified by silica gel column chromatography (DCM:MeOH=20:1) to afford benzyl (4-hydroxy-3,3-dimethylcyclohexyl)carbamate (110 g, 49.4%) as colorless oil.

Workup

  1. additionAfter addition
  2. filtrationThe mixture was filtered
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under vacuum
  8. customto give crude racemic product, which
  9. customwas purified by silica gel column chromatography (DCM:MeOH=20:1)

Sources & evidence

ORD record
ord-4d9eef34693249d1bce6fee54a22b88f
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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