Hydrochloric Acid → HCID 40630402, compound

HRID 272098Notes

Reaction equation

HRID 272098 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][C@H:3]([CH2:7][OH:8])[CH2:2]1.[CH:9]1([CH:15]=O)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.[Na].Cl>O1CCCC1.C(O)(=O)C>[CH:9]1([CH2:15][N:1]2[CH2:6][CH2:5][CH2:4][C@H:3]([CH2:7][OH:8])[CH2:2]2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 16275CyclohexanecarboxaldehydeHCID 853002((S)-piperidin-3-yl)methanolHCID 5360545Sodium

Product 1

HCID 40630402HCID 40630402, compoundYield 59.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 900 mg of (3S)-3-piperidylmethanol in 60 ml of tetrahydrofuran, 1.05 g of cyclohexanecarbaldehyde, 0.54 ml of acetic acid and 2.5 g of sodium triacetoxyborohydrate were successively added at room temperature by the order stated, followed by 21 hours' stirring at the same temperature. The reaction liquid was rendered acidic with 1N hydrochloric acid and washed with chloroform. The aqueous layer was rendered basic with 4N aqueous sodium hydroxide solution, followed by extraction with chloroform and drying over anhydrous sodium sulfate. Distilling the solvent off under reduced pressure, 990 mg of the title compound was obtained.

Workup

  1. customThe reaction liquid
  2. washwashed with chloroform
  3. extractionfollowed by extraction with chloroform
  4. dry with materialdrying over anhydrous sodium sulfate
  5. distillationDistilling the solvent off under reduced pressure

Sources & evidence

ORD record
ord-a3a312bcb7a9432e9e6758db323efcd2
Source dataset
uspto-grants-2008_11
Patent number
US07452908B2

Reaction notes

Loading…