(3R,4R)-benzyl 3-(tert-butoxycarbonylamino)-4-(methylsulfonyloxy)piperidine-1-carboxylate → HCID 58386792, compound

HRID 69996Notes

Reaction equation

HRID 69996 reaction equation
C([O:5][C:6]([NH:8][C@H:9]1[C@H:14](OS(C)(=O)=O)[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:7])(C)(C)C>N1C=CC=CC=1>[O:7]=[C:6]1[NH:8][C@@H:9]2[CH2:10][N:11]([C:20]([O:22][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[O:21])[CH2:12][CH2:13][C@@H:14]2[O:5]1

Participants

3

Reactant 1

HCID 58386823(3R,4R)-benzyl 3-(tert-butoxycarbonylamino)-4-(methylsulfonyloxy)piperidine-1-carboxylate

Product 1

HCID 58386792HCID 58386792, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of (3R,4R)-benzyl 3-(tert-butoxycarbonylamino)-4-(methylsulfonyloxy)piperidine-1-carboxylate in pyridine (0.16 M) was heated to 120° C. in the microwave for 10 minutes. The solution was then concentrated to almost dryness and the forming solid was filtered to give the desired product. The filtrate was further purified via silica gel column chromatography eluting with ethyl acetate (100%) to give the product in 75% combined yield. LCMS (m/z): 277.1 (MH+), LC Rt=2.33 min.

Workup

  1. concentrationThe solution was then concentrated to almost dryness
  2. filtrationthe forming solid was filtered

Sources & evidence

ORD record
ord-78e218876da94f89996a538f6001ce81
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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