Water → HCID 68973716, compound

HRID 238991Notes

Reaction equation

HRID 238991 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@H:10]([CH2:19]O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(S(F)(F)[F:27])CC)C.O>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@H:10]([CH2:19][F:27])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 123472(Diethylamino)sulfur trifluorideHCID 68973590HCID 68973590, compound

Product 1

HCID 68973716HCID 68973716, compoundYield 112.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

1.5 g trans-3-hydroxymethyl-4-phenyl-pyrrolidine-1-carboxylic acid tert-butyl ester (5.41 mmol) were dissolved in 20 ml dichloromethane and 1.31 g of diethylaminosulfurtrifluoride (DAST, 8.1 mmol) in 2 ml dichloromethane were added at 0° C. The reaction mixture was stirred for 72 h at room temperature, further dichloromethane and water were added, the organic phase was separated, dried over magnesium sulphate, filtered and evaporated to dryness to yield 1.7 g of a light yellowish oil. The crude product was purified via silica gel chromatography using n-heptane/ethyl acetate (6:4) as eluent to yield 1.08 g product.

Workup

  1. customthe organic phase was separated
  2. dry with materialdried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-cfffb1633c0f41b48c066e39bed0c5f1
Source dataset
uspto-grants-2014_02
Patent number
US08642642B2

Reaction notes

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