Sodium Hydroxide → (3S,4S)-benzyl 3-amino-4-cyclohexylpiperidine-1-carboxylate

HRID 1254411Notes

Reaction equation

HRID 1254411 reaction equation
C(OC([NH:8][C@H:9]1[C@H:14]([CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH2:13][CH2:12][N:11]([C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH2:10]1)=O)(C)(C)C.[OH-].[Na+]>Cl.C(#N)C>[NH2:8][C@H:9]1[C@H:14]([CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH2:13][CH2:12][N:11]([C:21]([O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:22])[CH2:10]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59382889HCID 59382889, compound

Product 1

HCID 59382981(3S,4S)-benzyl 3-amino-4-cyclohexylpiperidine-1-carboxylateYield 86.5%

Reagents, catalysts & solvents 1

HCID 22261314Acetonitrile--hydrogen chloride (1/1)Solvent

Procedure

(3S,4S)-benzyl 3-(tert-butoxycarbonylamino)-4-cyclohexylpiperidine-1-carboxylate (35 mg, 0.084 mmol) was dissolved in 1:1 2N aq HCl/acetonitrile (8 mL) and stirred overnight at rt. LC-MS showed the reaction was complete. The reaction mixture was basified with 5% aq NaOH solution to about pH=9. The acetonitrile was removed under vacuum. The aqueous residue was extracted with CH2Cl2 (3×20 mL). The combined organic layers were washed with brine (10 mL) and dried over Na2SO4. Concentration afforded (3S,4S)-benzyl 3-amino-4-cyclohexylpiperidine-1-carboxylate (23 mg, 86% yield). The crude product was used in the next step without further purification. LC-MS (3 min) tR=1.31 min., m/z 317 (M+1).

Workup

  1. customThe acetonitrile was removed under vacuum
  2. extractionThe aqueous residue was extracted with CH2Cl2 (3×20 mL)
  3. washThe combined organic layers were washed with brine (10 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationConcentration

Sources & evidence

ORD record
ord-60d0fe661baf4850a892be0287b7d5bb
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

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