Acetone → HCID 68766782, compound

HRID 1374374Notes

Reaction equation

HRID 1374374 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:16][CH2:15][N:14]([C@H:17]2[CH2:22][CH2:21][NH:20][CH2:19][C@H:18]2[C:23]([O:25][CH3:26])=[O:24])[C:13]1=[O:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:42][C:43]([CH3:45])=O.[OH-].[Na+]>C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:16][CH2:15][N:14]([CH:17]2[CH2:22][CH2:21][N:20]([CH:43]([CH3:45])[CH3:42])[CH2:19][CH:18]2[C:23]([O:25][CH3:26])=[O:24])[C:13]1=[O:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 68769573HCID 68769573, compound

Product 1

HCID 68766782HCID 68766782, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3R,4S)-Methyl 4-((3S)-3-(benzyloxycarbonylamino)-2-oxopyrrolidin-1-yl)piperidine-3-carboxylate (1.00 g, 2.66 mmol, 1 eq.), sodium triacetoxyborohydride (0.85 g, 4.00 mmol, 1.5 eq.) and acetone (0.59 mL, 7.99 mmol, 3 eq.) were mixed in methylene chloride (15 mL) and stirred for 20 hours at room temperature. Worked up by adding 20 mL of 1.000 N NaOH. Stirred 10 minutes then extracted 3 times with methylene chloride. The organic layers were combined, dried over sodium sulfate and stripped to give methyl 4-((3S)-3-(benzyloxycarbonylamino)-2-oxopyrrolidin-1-yl)-1-isopropyl-piperidine-3-carboxylate (1.10 g) of a white glass. Yield=99%. LCMS detects (M+H)+=418.41.

Workup

  1. stirringStirred 10 minutes
  2. extractionthen extracted 3 times with methylene chloride
  3. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-26f57f9118224be59e3f2159e5f1320d
Source dataset
uspto-grants-2007_01
Patent number
US07163937B2

Reaction notes

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