1,1-dimethylethyl (3S,4R)-4-hydroxy-3-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-piperidinecarboxylate → Phenylmethyl {[(3R,4R)-4-hydroxy-3-piperidinyl]methyl}carbamate

HRID 657139Notes

Reaction equation

HRID 657139 reaction equation
[OH:1][C@@H:2]1[CH2:7][CH2:6][N:5](C(OC(C)(C)C)=O)[CH2:4][C@@H:3]1[CH2:15][NH:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[OH:1][C@@H:2]1[CH2:7][CH2:6][NH:5][CH2:4][C@@H:3]1[CH2:15][NH:16][C:17](=[O:18])[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

3

Reactant 1

HCID 866353651,1-dimethylethyl (3S,4R)-4-hydroxy-3-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-piperidinecarboxylate

Product 1

HCID 86635366Phenylmethyl {[(3R,4R)-4-hydroxy-3-piperidinyl]methyl}carbamate

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

To a flask containing 1,1-dimethylethyl (3S,4R)-4-hydroxy-3-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-piperidinecarboxylate (E2)(500 mg; 1.37 mmol) was added 20 mL of TFA/DCM (50%). The reaction mixture was stirred for 1 h and then concentrated. The crude product was taken up in chloroform, treated with 500 mg of MP-carbonate resin (2.9 mmol/g) and stirred overnight. After filtration and concentration the product was obtained as its free base (370 mg; 100%).

Workup

  1. concentrationconcentrated
  2. additiontreated with 500 mg of MP-carbonate resin (2.9 mmol/g)
  3. stirringstirred overnight
  4. filtrationAfter filtration and concentration the product
  5. customwas obtained as its free base (370 mg; 100%)

Sources & evidence

ORD record
ord-187ae41911a44824ab54ec6322e2284b
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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