p-Toluenesulfonic acid → 3-((S)-1-cyclopentyloxycarbonyl-3-methyl-butylamino)-piperidine-1-carboxylic acid tert-butyl ester

HRID 632560Notes

Reaction equation

HRID 632560 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C:10](=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC1C=CC(S(O)(=O)=O)=CC=1.[CH:26]1([O:31][C:32](=[O:39])[C@@H:33]([NH2:38])[CH2:34][CH:35]([CH3:37])[CH3:36])[CH2:30][CH2:29][CH2:28][CH2:27]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClC(Cl)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([NH:38][C@H:33]([C:32]([O:31][CH:26]2[CH2:27][CH2:28][CH2:29][CH2:30]2)=[O:39])[CH2:34][CH:35]([CH3:37])[CH3:36])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 2756825Tert-butyl 3-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 53718217(S)-cyclopentyl 2-amino-4-methylpentanoate

Product 1

HCID 866864133-((S)-1-cyclopentyloxycarbonyl-3-methyl-butylamino)-piperidine-1-carboxylic acid tert-butyl esterYield 95.5%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 3-oxo-piperidine-1-carboxylic acid tert-butyl ester (0.458 g, 2.3 mmol) in dichloroethane (18 mL) was added the tosic acid salt of (S)-2-amino-4-methyl-pentanoic acid cyclopentyl ester (0.496 g, 2.53 mmol) and sodium triacetoxyborohydride (0.975 g, 4.6 mmol). The solution was stirred at room temperature for 18 hours. An aqueous solution of sodium hydrogen carbonate (20 mL) was added and the mixture stirred for 20 minutes. The desired product was extracted into ethyl acetate (3 times 15 mL). The organic layers were combined, dried (MgSO4) and concentrated to give the desired product (0.840 g, 95% yield) which was used without further purification. LC/MS: m/z 383 [M+H]+

Workup

  1. stirringthe mixture stirred for 20 minutes
  2. extractionThe desired product was extracted into ethyl acetate (3 times 15 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-01662dbdddfd4c719d0e62da3d54fcf8
Source dataset
uspto-grants-2016_04
Patent number
US09321718B2

Reaction notes

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