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Triphenylphosphine → (5S)-5-(Aminomethyl)-3-[4-(1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)-3,5-difluorophenyl]oxazolidin-2-one

HRID 1452603
Notes
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Reaction equation

HRID 1452603 reaction equation
[N:1]([CH2:4][C@@H:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[C:15]([F:17])[C:14]([C:18]3[CH2:19][CH2:20][N:21]([CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH2:22][CH:23]=3)=[C:13]([F:31])[CH:12]=2)[CH2:6]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C.O>[NH2:1][CH2:4][C@@H:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[C:15]([F:17])[C:14]([C:18]3[CH2:19][CH2:20][N:21]([CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH2:22][CH:23]=3)=[C:13]([F:31])[CH:12]=2)[CH2:6]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 86598354(5R)-5-(Azidomethyl)-3-[4-(1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)-3,5-difluorophenyl]-1,3-oxazolidin-2-one

Product 1

HCID 57526982(5S)-5-(Aminomethyl)-3-[4-(1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)-3,5-difluorophenyl]oxazolidin-2-oneYield 70.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 6342
Acetonitrile
Solvent

Procedure

(5R)-5-(Azidomethyl)-3-[4-(1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)-3,5-difluorophenyl]-1,3-oxazolidin-2-one (WO 0181350) (10.60 g, 24.97 mmol) was dissolved in acetonitrile (250 ml) and water (25 ml). Triphenylphosphine (7.86 g, 29.96 mmol) was added and the suspension was stirred at room temperature for approximately 16 h. The reaction mixture was concentrated under vacuum. The crude material was purified by chromatography on silica gel using 2.5-5% methanol in dichloromethane to give 7.03 g of the title product.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customThe crude material was purified by chromatography on silica gel using 2.5-5% methanol in dichloromethane

Sources & evidence

ORD record
ord-2fb3db54bead4f81b704fc5465396240
Source dataset
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07473699B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes