2,2-Dimethoxypropane → tert-Butyl (S)-4-(4-hydroxybenzyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

HRID 1669501Notes

Reaction equation

HRID 1669501 reaction equation
[C:1]([NH:8][C@H:9]([CH2:18][OH:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CO[C:22](OC)([CH3:24])[CH3:23]>C1(C)C=CC(S(O)(=O)=O)=CC=1.ClCCl>[C:4]([O:3][C:1]([N:8]1[C@@H:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)[CH2:18][O:19][C:22]1([CH3:24])[CH3:23])=[O:2])([CH3:5])([CH3:7])[CH3:6]

Participants

5

Reactant 2

HCID 64952,2-DimethoxypropaneHCID 15934817tert-butyl N-((2S)-1-hydroxy-3-(4-hydroxyphenyl)propan-2-yl)carbamate

Product 1

HCID 10425336tert-Butyl (S)-4-(4-hydroxybenzyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylateYield 83%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of Boc-L-Tyrosinol (1 g, 3.74 mmol), p-toluenesulfonic acid (0.0356 g, 0.187 mmol), and dichloromethane (DCM) (7.66 mL) was added 2,2 dimethoxypropane (2.3 mL, 18.7 mmol). The resulting mixture was stirred overnight at room temperature under nitrogen. Reaction mixture was washed with sodium bicarbonate (20 mL). Organic layer was separated and washed with sodium bicarbonate (20 mL). The sodium bicarbonate layers were combined and washed with DCM (20 mL). DCM layers were combined, dried over MgSO4, filtered, and concentrated in vacuo to obtain a crude mixture that was purified by silica gel flash chromatography, using EtOAc/hexane (gradient system) to obtain product (0.87 g, 83%): 1H NMR (400 MHz, CDCL3): δ 1.42-1.68 (m, 15H), 2.57-2.63 (m, 1H), 3.00-3.14 (m, 1H), 3.74-3.80 (m, 2H), 3.91-4.05 (m, 1H), 6.77 (t, 2H, J=8.8 Hz), 7.08 (dd, 1H, J=8.0 Hz, J=16 Hz).

Workup

  1. customReaction mixture
  2. washwas washed with sodium bicarbonate (20 mL)
  3. customOrganic layer was separated
  4. washwashed with sodium bicarbonate (20 mL)
  5. washwashed with DCM (20 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto obtain a crude mixture that
  10. customwas purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-042d250059204e6aa413fac8f7ceb50f
Source dataset
uspto-grants-2011_08
Patent number
US07989480B2

Reaction notes

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