Dimethyl Sulfide → Cbz-L-Prolinol

HRID 21766

Reaction equation

HRID 21766 reaction equation
[C:1]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13](O)=[O:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].CSC>C1COCC1>[C:1]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[CH2:13][OH:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

4

Reactant 2

HCID 1068Dimethyl SulfideHCID 101987Benzyloxycarbonyl-L-proline

Product 1

HCID 11096562Cbz-L-ProlinolYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A 21.56 g (86.55 mmol) sample of the compound from step 24a above was dissolved in 200 mL of THF, and the solution was cooled to 0° C. BH3 -dimethyl sulfide (86.5 mL, 2N) was added dropwise under a nitrogen atmosphere. The reaction was stirred at room temperature for 16 hr, then cooled to 0° C. and quenched by careful addition of 10% acetic acid in methanol. The mixture was reduced in volume on a rotary evaporator, and the concentrate was dissolved in ethyl acetate, which was washed successively with 1N HCl, water and sodium bicarbonate solution. The organic extract was dried over Na2SO4 and concentrated to afford the title product, 19.94 g (98% yield).

Workup

  1. temperaturecooled to 0° C.
  2. customquenched by careful addition of 10% acetic acid in methanol
  3. customThe mixture was reduced in volume on a rotary evaporator
  4. dissolutionthe concentrate was dissolved in ethyl acetate
  5. washwhich was washed successively with 1N HCl, water and sodium bicarbonate solution
  6. extractionThe organic extract
  7. dry with materialwas dried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b7584f1f3ebc4e52879c9f889abda715
Source dataset
uspto-grants-1995_06
Patent number
US05424444

Linked notes

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