2-Methoxypropene → Tert-butyl 4-(2-benzyloxymethyl-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 252404Notes

Reaction equation

HRID 252404 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([CH:23]([CH3:25])[CH3:24])[CH2:11][CH: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][CH:10]([CH:23]([CH3:25])[CH3:24])[CH2:11][CH: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 77887193Tert-butyl (3-benzyloxymethyl-1-hydroxymethyl-4-methylpentyl)carbamate

Product 1

HCID 66887921Tert-butyl 4-(2-benzyloxymethyl-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 14.70 g of tert-butyl (3-benzyloxymethyl-1-hydroxymethyl-4-methylpentyl)carbamate and 0.24 g of p-toluenesulphonic acid monohydrate in 82 ml of dichloromethane at 0° C. is admixed with 8.2 ml of 2-methoxypropene. After 22 hours at room temperature, the mixture is poured onto 1M aqueous sodium hydrogencarbonate solution and 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 as an orange oil from the residue by means of flash chromatography (SiO2 60F). Rt=6.30 (gradient I).

Workup

  1. customat 0° C.
  2. extractionextracted with tert-butyl methyl ether (2×)—the combined organic phases
  3. washare washed with brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-d34684c44c38468f81d0c1b745f754c5
Source dataset
uspto-grants-2011_01
Patent number
US07868036B2

Reaction notes

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