Methanol → (R)-3-chlorocarbonyl-piperidine-1-carboxylic acid benzyl ester

HRID 1020060Notes

Reaction equation

HRID 1020060 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][C@@H:13]([C:17]([OH:19])=O)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C=O)C.CO.C(Cl)(=O)C([Cl:30])=O>>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][C@@H:13]([C:17]([Cl:30])=[O:19])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 7365381-(Phenylmethyl) (3R)-1,3-piperidinedicarboxylate

Product 1

HCID 7145254(R)-3-chlorocarbonyl-piperidine-1-carboxylic acid benzyl ester

Procedure

(R)-Piperidine-1,3-dicarboxylic acid 1-benzyl ester (XXVIII) (8.00 g, 30.4 mmol) was taken in neat oxalyl chloride (20 ml), 0.2 ml of DMF were added and the mixture was stirred at room temperature for 1 hour. The completion of reaction was monitored by TLC which showed the formation of a non-polar spot after treatment of a small amount with methanol. The reaction mixture was concentrated under reduced pressure to provide (R)-3-chlorocarbonyl-piperidine-1-carboxylic acid benzyl ester (XXIX) (8.33 g) which was directly used in the next reaction.

Workup

  1. customThe completion of reaction
  2. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a0f67a526b71402a9589730ea5c62580
Source dataset
uspto-grants-2014_05
Patent number
US08716296B2

Reaction notes

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