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Ethyl benzylcarbamate → (5R)-3-(4-(1-benzyl-1,2,5,6-tetrahydropyridin-4-yl)-3,5-difluorophenyl)-5-hydroxymethyloxazolidin-2-one

HRID 1167418
Notes
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Reaction equation

HRID 1167418 reaction equation
C(N[C:9]([O:11][CH2:12][CH3:13])=[O:10])C1C=CC=CC=1.[F:14][C:15]1[CH:16]=[C:17]([CH:19]=[C:20]([F:35])[C:21]=1[C:22]1[CH2:27][CH2:26][N:25]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:24][CH:23]=1)[NH2:18].[Li]CCCC.[C:41](OC[C@@H]1OC1)(=[O:45])CCC>C1COCC1>[OH:45][CH2:41][C@@H:12]1[O:11][C:9](=[O:10])[N:18]([C:17]2[CH:19]=[C:20]([F:35])[C:21]([C:22]3[CH2:27][CH2:26][N:25]([CH2:28][C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH2:24][CH:23]=3)=[C:15]([F:14])[CH:16]=2)[CH2:13]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 75801Ethyl benzylcarbamateHCID 2724536(2R)-Oxiran-2-ylmethyl butanoateHCID 114834303,5-Difluoro-4-(1-benzyl-1,2,5,6-tetrahydropyrid-4-yl)anilineHCID 178418339Butyllithium

Product 1

HCID 11304129(5R)-3-(4-(1-benzyl-1,2,5,6-tetrahydropyridin-4-yl)-3,5-difluorophenyl)-5-hydroxymethyloxazolidin-2-oneYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

The benzylurethane from Reference Example 3 (5.54 g, 12.76 mmol ) in 50 ml dry THF was cooled to −70° C. under nitrogen and 8.80 ml of 1.6M nBuLi in hexanes (14.08 mmol ) added dropwise at the same temperature. After 20 minutes at the same temperature a solution of (R)-glycidyl butyrate (2.00 g, 13.88 mmol in 5 ml THF) was added dropwise and the mixture stirred for 30 minutes at −70° C., and then stirred to ambient temperature overnight. After quenching with 100 ml 10% ammonium chloride, the mixture was extracted with EtOAc and usual work-up to give an oily solid, which was purified by flash chromatography (Merck C60 silica, 5% MeOH/dichloromethane eluant) to give a crystalline solid (4.40 g, 86%). MS: ESP+ (M+H)=401.

Workup

  1. customwas cooled to −70° C. under nitrogen
  2. stirringstirred to ambient temperature overnight
  3. customAfter quenching with 100 ml 10% ammonium chloride
  4. extractionthe mixture was extracted with EtOAc and usual work-up
  5. customto give an oily solid, which
  6. customwas purified by flash chromatography (Merck C60 silica, 5% MeOH/dichloromethane eluant)

Sources & evidence

ORD record
ord-e00550519c354f67a43474e1befba37f
Source dataset
uspto-grants-2003_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06617339B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes