2-Methoxypropene → tert-Butyl 4(S)-(2(S)-benzyloxymethyl-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 507835Notes

Reaction equation

HRID 507835 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]([CH:23]([CH3:25])[CH3:24])[CH2:11][C@H:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:13][OH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[C:27]1(C)[CH:32]=CC(S(O)(=O)=O)=C[CH:28]=1.COC(C)=C.C(=O)([O-])O.[Na+]>ClCCl>[CH2:1]([O:8][CH2:9][C@H:10]([CH:23]([CH3:25])[CH3:24])[CH2:11][C@H:12]1[CH2:13][O:14][C:27]([CH3:32])([CH3:28])[N:15]1[C:16]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 83002-MethoxypropeneHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 70642503tert-butyl (2S,4S)-4-(benzyloxymethyl)-1-hydroxy-5-methylhexan-2-ylcarbamate

Product 1

HCID 68624760tert-Butyl 4(S)-(2(S)-benzyloxymethyl-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The solution of 3.51 g of tert-butyl (3(S)-benzyloxymethyl-1(S)-hydroxymethyl-4-methyl-pentyl)carbamate in 20 ml of dichloromethane is cooled to 0° C. and admixed successively with 0.076 g of p-toluenesulphonic acid monohydrate and 2.6 ml of 2-methoxypropene. The reaction mixture is stirred at room temperature for another 16 hours and subsequently poured onto 1M sodium hydrogencarbonate solution, extracted with tert-butyl methyl ether (2×). The combined organic phases are washed with brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F) as a yellowish oil. Rf=0.42 (1:4 EtOAc-heptane); Rt=6.20 (gradient I).

Workup

  1. extractionextracted with tert-butyl methyl ether (2×)
  2. washThe combined organic phases are washed with brine
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-b9114307897844bfbdd5fe8805f70277
Source dataset
uspto-grants-2010_08
Patent number
US07786307B2

Reaction notes

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