2,2-Dimethoxypropane → (RS)-4-(4-iodo-phenyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

HRID 1805212Notes

Reaction equation

HRID 1805212 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][CH:8]([C:11]1[CH:16]=[CH:15][C:14]([I:17])=[CH:13][CH:12]=1)[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].CO[C:21](OC)([CH3:23])[CH3:22].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl>[C:1]([O:5][C:6]([N:7]1[CH:8]([C:11]2[CH:16]=[CH:15][C:14]([I:17])=[CH:13][CH:12]=2)[CH2:9][O:10][C:21]1([CH3:23])[CH3:22])=[O:18])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 64952,2-DimethoxypropaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 67151743n-Boc-[2-hydroxy-1-(4-iodophenyl)ethyl]-amine

Product 1

HCID 67151644(RS)-4-(4-iodo-phenyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl esterYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (RS)-[2-hydroxy-1-(4-iodo-phenyl)-ethyl]-carbamic acid tert-butyl ester (7.97 g) in dichloromethane (400 ml) were added sequentially 2,2-dimethoxypropane (36 ml) and p-toluenesulphonic acid monohydrate (0.75 g) and the mixture was stirred at room temperature for 18 hours. The mixture was then washed with 0.5 N aq NaOH, the phases were separated and the organic phase was dried over sodium sulphate, filtered and concentrated in vacuo to afford (RS)-4-(4-iodo-phenyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (7.05 g, 89%) as a yellow solid. MS (EI): 403 (M+), 388 ([M-CH3]+), 332 ([M-CH3—C4H8]+), 288 ([M-CH3—C4H8—CO2]+), 57 ([C4H9]+).

Workup

  1. washThe mixture was then washed with 0.5 N aq NaOH
  2. customthe phases were separated
  3. dry with materialthe organic phase was dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b6fdfb1ceb0049eab88a3d6af6ca74b1
Source dataset
uspto-grants-2013_01
Patent number
US08354441B2

Reaction notes

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