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

HRID 657145Notes

Reaction equation

HRID 657145 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 866353641,1-dimethylethyl (3R,4S)-4-hydroxy-3-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-piperidinecarboxylate

Product 1

HCID 86635369Phenylmethyl {[(3S,4S)-4-hydroxy-3-piperidinyl]methyl}carbamateYield 84%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

To a flask containing 1,1-dimethylethyl (3R,4S)-4-hydroxy-3-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-piperidinecarboxylate (for a preparation see Example 135(e)) (1 g; 2.74 mmol) was added 100 mL of TFA/DCM (50%). The reaction mixture was stirred for 1 h and then concentrated. The crude product was made basic by the addition of 6N NaOH and extracted into 10% MeOH/DCM (2×50 mL). The organic fractions were dried with anhydrous sodium sulfate, filtered and concentrated to obtain the product as a clear oil (607 mg; 84%).

Workup

  1. concentrationconcentrated
  2. additionThe crude product was made basic by the addition of 6N NaOH
  3. extractionextracted into 10% MeOH/DCM (2×50 mL)
  4. dry with materialThe organic fractions were dried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-63d778db94db4a9282cc1c20d7cf3f6a
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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