Dichloromethane → 2-benzyl 3-methyl (2S,3S,5S)-1-benzyl-5-[(pyrrolidin-1-ylcarbonyl)oxy]piperidine-2,3-dicarboxylate

HRID 61461Notes

Reaction equation

HRID 61461 reaction equation
[CH2:1]([N:8]1[CH2:13][C@@H:12]([OH:14])[CH2:11][C@H:10]([C:15]([O:17][CH3:18])=[O:16])[C@H:9]1[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)Cl.C1N=CN([C:37]([N:39]2[CH:43]=N[CH:41]=[CH:40]2)=[O:38])C=1.N1CCC[CH2:45]1>>[CH2:1]([N:8]1[CH2:13][C@@H:12]([O:14][C:37]([N:39]2[CH2:40][CH2:41][CH2:45][CH2:43]2)=[O:38])[CH2:11][C@H:10]([C:15]([O:17][CH3:18])=[O:16])[C@H:9]1[C:19]([O:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 31268PyrrolidineHCID 682631,1'-CarbonyldiimidazoleHCID 866214902-benzyl 3-methyl(2S,3S,5S)-1-benzyl-5-hydroxypiperidine-2,3-dicarboxylate

Product 1

HCID 1317319292-benzyl 3-methyl (2S,3S,5S)-1-benzyl-5-[(pyrrolidin-1-ylcarbonyl)oxy]piperidine-2,3-dicarboxylateYield 88.7%

Procedure

To a solution of 2-benzyl 3-methyl(2S,3S,5S)-1-benzyl-5-hydroxypiperidine-2,3-dicarboxylate (144 mg, 0.000376 mol) in methylene chloride (2.0 mL, 0.031 mol) was added N,N-carbonyldiimidazole (73.1 mg, 0.000451 mol). The reaction was stirred at rt for 2 h. To the resulting mixture was added pyrrolidine (0.0470 mL, 0.000563 mol) and the reaction was stirred at rt overnight. The reaction was quenched with aq sodium bicarbonate, extracted with methylene chloride. The combined organic layers were dried, purified on silica gel (eluting with 0 to 40% EtOAc in hexane) to provide the carbamate compound (160 mg, 88.7%). MS (ESI): (M+H)+=481.2.

Workup

  1. stirringthe reaction was stirred at rt overnight
  2. customThe reaction was quenched with aq sodium bicarbonate
  3. extractionextracted with methylene chloride
  4. customThe combined organic layers were dried
  5. custompurified on silica gel (eluting with 0 to 40% EtOAc in hexane)

Sources & evidence

ORD record
ord-f324202f364e465388b3c6a77b2dc235
Source dataset
uspto-grants-2016_09
Patent number
US09440958B2

Reaction notes

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