Sodium Bicarbonate → tert-Butyl-(4S)-4-(1-fluoroprop-2-en-1-yl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

HRID 2101664Notes

Reaction equation

HRID 2101664 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:12]([CH:13]=[CH:14][CH2:15][Si](C)(C)C)[CH2:11][O:10][C:9]1([CH3:21])[CH3:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].[B-](F)(F)(F)[F:23].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1.C([O-])(O)=O.[Na+]>C(#N)C>[C:1]([O:5][C:6]([N:8]1[C@H:12]([CH:13]([F:23])[CH:14]=[CH2:15])[CH2:11][O:10][C:9]1([CH3:21])[CH3:20])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724933SelectfluorHCID 68858073Tert-butyl-(4r)-2,2-dimethyl-4-(3-trimethylsilanyl-propenyl)-1,3-oxazolidine-3-carboxylate

Product 1

HCID 57801768tert-Butyl-(4S)-4-(1-fluoroprop-2-en-1-yl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylateYield 72%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of the compound produced in Example 47 (0.196 g, 0.63 mmol) in acetonitrile (6 ml), was added Selectfluor™ (0.33 g, 1.5 eq.) and NaHCO3 (0.105 g, 2 eq.). The reaction mixture was stirred under an atmosphere of nitrogen for 20 hours before concentrating under reduced pressure. Purification by flash chromatography (diethyl ether:hexane 1:19) afforded the product (0.116 g, 72%). de=33%.

Workup

  1. concentrationbefore concentrating under reduced pressure
  2. customPurification by flash chromatography (diethyl ether:hexane 1:19)

Sources & evidence

ORD record
ord-6d55359d03c9469ebf2fb3a0d505af62
Source dataset
uspto-grants-2009_08
Patent number
US07572928B2

Reaction notes

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