HCID 178418435, compound → HCID 178523769, compound

HRID 722026Notes

Reaction equation

HRID 722026 reaction equation
B.[Na].[CH2:3]([O:10][C:11]([NH:13][C@H:14]1[CH2:19][CH2:18][C@H:17]([C:20](O)=[O:21])[CH2:16][CH2:15]1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O1CCCC1>[CH2:3]([O:10][C:11]([NH:13][C@H:14]1[CH2:19][CH2:18][C@H:17]([CH2:20][OH:21])[CH2:16][CH2:15]1)=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 178418435HCID 178418435, compoundHCID 178523781HCID 178523781, compound

Product 1

HCID 178523769HCID 178523769, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 35 ml of tetrahydrofuran was suspended 0.74 g of sodium boron hydride, and boron trifluoride diethyl complex was added to the suspension under ice-cooling. The mixture was stirred as such under ice-cooling for 30 minutes, and 90 ml of a tetrahydrofuran solution containing 3.60 g of trans-4-(benzyloxycarbonylamino)cyclohexanecarboxylic acid was added thereto under ice-cooling. After the mixture was stirred at room temperature for 2 hours, the reaction mixture was poured into an ice water and extracted with chloroform. The extract was washed with water and brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was suspended in diisopropyl ether and collected by filtration to obtain N-benzyloxycarbonyl-trans-4-(hydroxymethyl)cyclohexylamine.

Workup

  1. additionwas added to the suspension under ice-
  2. temperaturecooling
  3. temperaturecooling for 30 minutes
  4. additionwas added
  5. temperatureunder ice-cooling
  6. stirringAfter the mixture was stirred at room temperature for 2 hours
  7. extractionextracted with chloroform
  8. washThe extract was washed with water and brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. customthe solvent was removed under reduced pressure
  11. filtrationcollected by filtration

Sources & evidence

ORD record
ord-c758da7d41784db6af8fd7bdd45166f8
Source dataset
uspto-grants-2006_11
Patent number
US07138397B2

Reaction notes

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