Oxalic Acid → Benzyl 5-[(benzyloxy)amino]piperidine-2-carboxylate ethanedioate

HRID 508457Notes

Reaction equation

HRID 508457 reaction equation
[CH2:1]([O:8][C:9]([CH:11]1[CH2:16][CH2:15][CH:14]([NH:17][O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:13][NH:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26]([OH:31])(=[O:30])[C:27]([OH:29])=[O:28]>C(O)(C)C>[C:26]([OH:31])(=[O:30])[C:27]([OH:29])=[O:28].[CH2:1]([O:8][C:9]([CH:11]1[CH2:16][CH2:15][CH:14]([NH:17][O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:13][NH:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 74928887Phenylmethyl 5-[(phenylmethoxy)amino]-2-piperidinecarboxylate

Product 1

HCID 77895673Benzyl 5-[(benzyloxy)amino]piperidine-2-carboxylate ethanedioateYield 87%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To 5-benzyloxyamino-piperidine-2-carboxylic acid benzyl ester (0.857 g, 2.51 mmol) having diastereo ratio of (2S,5R)/(2S,5S)=77.4/22.6 (54.8% de), isopropanol (4.86 g) and oxalic acid (0.227 g, 2.52 mmol) were added, and the obtained mixture was stirred for 2 hours. The precipitate was filtrated, and washed with isopropanol (0.83 g) for 2 times, and dried at 50° C. under reduced pressure to obtain 5-benzyloxyamino-piperidine-2-carboxylic acid benzyl ester oxalate (0.937 g, 2.18 mmol, yield: 87%). The diastereo ratio of this solid was (2S,5R)/(2S,5S)=88.4/11.6 (76.7% de).

Workup

  1. additionwere added
  2. filtrationThe precipitate was filtrated
  3. washwashed with isopropanol (0.83 g) for 2 times
  4. customdried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-6dbcc6f5bab6473aa39485b8728692e7
Source dataset
uspto-grants-2015_08
Patent number
US09096523B2

Reaction notes

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