Triethylamine → HCID 14629887, compound

HRID 1683391Notes

Reaction equation

HRID 1683391 reaction equation
[C:1]1([CH2:7][O:8][C:9]([N:11]2[CH2:15][CH2:14][CH2:13][C@H:12]2[CH2:16][OH:17])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:18][C:19]([Si:22](Cl)([CH3:24])[CH3:23])([CH3:21])[CH3:20].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:1]1([CH2:7][O:8][C:9]([N:11]2[CH2:15][CH2:14][CH2:13][C@H:12]2[CH2:16][O:17][Si:22]([C:19]([CH3:21])([CH3:20])[CH3:18])([CH3:24])[CH3:23])=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 11096562Cbz-L-Prolinol

Product 1

HCID 14629887HCID 14629887, compoundYield 88.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution 58.0 g of (S)-2-hydroxymethyl-1-pyrrolidine carboxylic acid phenylmethyl ester, 45.0 g of (1,1-dimethylethyl)dimethylsilylchloride, 69 ml of triethylamine, 1.50 g of 4-(dimethylamino)pyridine and 450 ml of methylene chloride is stirred at room temperature for 18 hours. The resulting solution is washed with water, 2N hydrochloric acid, saturated sodium bicarbonate and sodium chloride. The organic layer is dried and concentrated in vacuo. The residue, dissolved in methylene chloride, is filtered through a silica gel pad and concentrated in vacuo to give 76.5 g of the desired product as a colorless oil.

Workup

  1. washThe resulting solution is washed with water, 2N hydrochloric acid, saturated sodium bicarbonate and sodium chloride
  2. customThe organic layer is dried
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue, dissolved in methylene chloride
  5. filtrationis filtered through a silica gel pad
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4010875894c1445ca1f7a9dc9ab868e1
Source dataset
uspto-grants-1997_06
Patent number
US05637731

Reaction notes

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