2-Propanethiol → (2S)-1-(t-Butoxycarbonyl)-2-[1-hydroxy-2-(isopropylthio)-ethyl]pyrrolidine

HRID 1720484Notes

Reaction equation

HRID 1720484 reaction equation
[CH:1]([SH:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:12]([O:16][C:17]([N:19]1[CH2:23][CH2:22][CH2:21][C@H:20]1[CH:24]1[O:26][CH2:25]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]>CO>[C:12]([O:16][C:17]([N:19]1[CH2:23][CH2:22][CH2:21][C@H:20]1[CH:24]([OH:26])[CH2:25][S:4][CH:1]([CH3:3])[CH3:2])=[O:18])([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 63642-PropanethiolHCID 8471TriethylamineHCID 15297813tert-butyl (2S)-2-(oxiran-2-yl)pyrrolidine-1-carboxylate

Product 1

HCID 22860063(2S)-1-(t-Butoxycarbonyl)-2-[1-hydroxy-2-(isopropylthio)-ethyl]pyrrolidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Isopropylmercaptan (0.93 ml) and triethylamine (1.39 ml) were added to (2S)-1-(t-butoxycarbonyl)-2-(1,2-epoxyethyl)-pyrrolidine (2.11 g) as obtained in Example 1-A) in methanol (100 ml), and the mixture was stirred for 2 hours under reflux. The reaction mixture was concentrated and the residue was purified by silica gel column chromatography (eluate: hexane-ethyl acetate) to give 1.66 g of the title compound.

Workup

  1. temperatureunder reflux
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by silica gel column chromatography (eluate: hexane-ethyl acetate)

Sources & evidence

ORD record
ord-ea59e30d9d0d4a938ef070387cb8f28b
Source dataset
uspto-grants-1996_04
Patent number
US05506256

Reaction notes

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