Sodium Hydroxide → HCID 59201572, compound

HRID 451804Notes

Reaction equation

HRID 451804 reaction equation
C(OC([NH:8][C@H:9]1[C@H:14]([CH2:15][CH:16]2[CH2:19][CH2:18][CH2:17]2)[CH2:13][CH2:12][N:11]([C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])[CH2:10]1)=O)(C)(C)C.[OH-].[Na+]>Cl.C(#N)C>[NH2:8][C@H:9]1[C@H:14]([CH2:15][CH:16]2[CH2:19][CH2:18][CH2:17]2)[CH2:13][CH2:12][N:11]([C:20]([O:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[O:21])[CH2:10]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59201519HCID 59201519, compound

Product 1

HCID 59201572HCID 59201572, compoundYield 85%

Reagents, catalysts & solvents 1

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

Procedure

(±)-trans-benzyl 3-(tert-butoxycarbonylamino)-4-(cyclobutylmethyl)piperidine-1-carboxylate (14 mg, 0.035 mmol)) was dissolved in 1:1 2N aq HCl/acetonitrile (8 mL) and stirred overnight at rt. 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 (±)-trans-benzyl 3-amino-4-(cyclobutylmethyl)piperidine-1-carboxylate (8.9 mg, 85% yield). The crude product was used in the next step without further purification. MS ESI +ve m/z 303 (M+Na).

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-85003e430a10499095715f4eb4166d33
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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