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

HRID 1920189Notes

Reaction equation

HRID 1920189 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 yield (3aR,7aS)-benzyl 2-oxohexahydrooxazolo[4,5-c]pyridine-5(6H)-carboxylate in 75% combined yield. LCMS (m/z): 277.1 (MH+), Rt=2.327 min.

Workup

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

Sources & evidence

ORD record
ord-376d853a1f454988ab5b17e67a1d7651
Source dataset
uspto-grants-2012_05
Patent number
US08168794B2

Reaction notes

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