Hydrochloric Acid → HCID 40630402, compound

HRID 394050Notes

Reaction equation

HRID 394050 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.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[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 5049666Sodium triacetoxyborohydride

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 triacetoxyborohydride 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-fbe51063b27a459b989017cbd8676928
Source dataset
uspto-grants-2004_10
Patent number
US06809108B1

Reaction notes

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