HCID 178418435, compound → HCID 178453956, compound

HRID 1445360Notes

Reaction equation

HRID 1445360 reaction equation
B.[Na].[C:3]([O:7][C:8]([NH:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([C:17](O)=[O:18])[CH2:13][CH2:12]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>O1CCCC1>[C:3]([O:7][C:8]([NH:10][C@H:11]1[CH2:12][CH2:13][C@H:14]([CH2:17][OH:18])[CH2:15][CH2:16]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 178418435HCID 178418435, compoundHCID 178453972HCID 178453972, compound

Product 1

HCID 178453956HCID 178453956, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

9.33 g of sodium boron hydride was suspended in 200 ml of tetrahydrofuran, and added thereto was boron trifluoride diethyl complex under ice-cooling. The mixture was stirred as such under ice-cooling for 30 minutes, and then, 150 ml of a tetrahydrofuran solution containing 40 g of trans-4-(tert-butoxycarbonylamino)cyclohexane carboxylic acid was added thereto under ice-cooling. The mixture was stirred at room temperature for 4 hours, and the reaction mixture was poured into 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 recrystallized from ethyl acetate-hexane to obtain 20 g of N-tert-butoxycarbonyl-trans-4-(hydroxymethyl)cyclohexylamine. (2) By using the compound obtained in the above (1) and corresponding starting materials, compounds of Reference Examples 9-14 to 9-29 in Table 10 were obtained in the same manner as in Reference Example 9-8.

Workup

  1. additionadded
  2. temperaturecooling
  3. temperaturecooling for 30 minutes
  4. additionwas added
  5. temperatureunder ice-cooling
  6. stirringThe mixture was stirred at room temperature for 4 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. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-6470d3f3388346e7a64c0c275e1a9b7d
Source dataset
uspto-grants-2010_02
Patent number
US07666869B2

Reaction notes

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