Piperidine → HCID 68818214, compound

HRID 732606Notes

Reaction equation

HRID 732606 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:7]([O:11][C:12]([N:14]1[CH2:18][CH:17]([CH2:19][C:20](O)=[O:21])[CH2:16][C@@H:15]1[C@H:23]1[O:27][C:26]([CH3:29])([CH3:28])[N:25]([C:30](=[O:32])[CH3:31])[C@H:24]1[CH2:33][C:34]1[CH:39]=[C:38]([F:40])[CH:37]=[C:36]([F:41])[CH:35]=1)=[O:13])([CH3:10])([CH3:9])[CH3:8].F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.CN(C1C=CC=CN=1)C.C(N(CC)CC)C>ClCCl>[C:7]([O:11][C:12]([N:14]1[CH2:18][CH:17]([CH2:19][C:20](=[O:21])[N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:16][C@@H:15]1[C@H:23]1[O:27][C:26]([CH3:29])([CH3:28])[N:25]([C:30](=[O:32])[CH3:31])[C@H:24]1[CH2:33][C:34]1[CH:35]=[C:36]([F:41])[CH:37]=[C:38]([F:40])[CH:39]=1)=[O:13])([CH3:8])([CH3:9])[CH3:10]

Participants

7

Reactant 5

HCID 8082PiperidineHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 2733179PyBroPHCID 68814269HCID 68814269, compound

Product 1

HCID 68818214HCID 68818214, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add piperidine (0.013 g, 0.151 mmol) to a solution of (R)-2-[(4S,5S)-3-Acetyl-4-(3,5-difluoro-benzyl)-2,2-dimethyl-oxazolidin-5-yl]-4-carboxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (mixture of isomers) (0.05 g, 0.101 mmol), bromo tris-pyrrolidinophosphonium hexafluorophosphate (0.094 g, 0.201 mmol), dimethylamino-pyridine (0.001 g, 0.01 mmol) and triethylamine (0.021 mL, 0.151 mmol) in 2.2 mL of dichloromethane. Stir the reaction overnight. Concentrate under reduced pressure and subject the residue to silica gel chromatography, eluting with hexane/ethyl acetate (70% gradient to 100%) to provide both isomers of the desired compound. The 4(R) isomer is the slower eluting (0.033 g, 60%).

Workup

  1. customthe reaction overnight
  2. concentrationConcentrate under reduced pressure
  3. washeluting with hexane/ethyl acetate (70% gradient to 100%)

Sources & evidence

ORD record
ord-ea755dcfa42245f1b1fc35a96b6fb7e9
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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