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

HRID 508455Notes

Reaction equation

HRID 508455 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[CH2:7]([O:14][C:15]([CH:17]1[CH2:22][CH2:21][CH:20]([NH:23][O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:19][NH:18]1)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CO>[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[CH2:7]([O:14][C:15]([CH:17]1[CH2:22][CH2:21][CH:20]([NH:23][O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:19][NH:18]1)=[O:16])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=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 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methanol (4.78 g) and oxalic acid (0.219 g, 2.43 mmol) was added to 5-benzyloxyamino-piperidine-2-carboxylic acid benzyl ester (0.804 g, 2.36 mmol) having diastereo ratio of (2S,5R)/(2S,5S)=77.4/22.6 (54.8% de), and the obtained mixture was stirred for 2 hours. The precipitate was filtrated, washed with methanol (0.80 g) for 2 times, and dried at 50° C. under reduced pressure to obtain 5-benzyloxyamino-piperidine-2-carboxylic acid benzyl ester oxalate (0.556 g, 1.29 mmol, yield: 55%). The diastereo ratio of this solid was (2S,5R)/(2S,5S)=99.1/0.9 (98.2 ode).

Workup

  1. filtrationThe precipitate was filtrated
  2. washwashed with methanol (0.80 g) for 2 times
  3. customdried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-c745864f1a4a42babf750d8442f50f8b
Source dataset
uspto-grants-2015_08
Patent number
US09096523B2

Reaction notes

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