Piperidine → (S)-2-Amino-3-tert-butylsulfanyl-propionic acid cyclopentyl ester

HRID 548218Notes

Reaction equation

HRID 548218 reaction equation
[CH:1]1([O:6][C:7](=[O:33])[C@H:8]([NH:15]C(OCC2C3C=CC=CC=3C3C2=CC=CC=3)=O)[CH2:9][S:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:5][CH2:4][CH2:3][CH2:2]1.N1CCCCC1>CC#N>[CH:1]1([O:6][C:7](=[O:33])[C@H:8]([NH2:15])[CH2:9][S:10][C:11]([CH3:12])([CH3:13])[CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 57971729(S)-3-tert-Butylsulfanyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid cyclopentyl ester

Product 1

HCID 57971616(S)-2-Amino-3-tert-butylsulfanyl-propionic acid cyclopentyl esterYield 73.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(S)-3-tert-Butylsulfanyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid cyclopentyl ester (1.63 g, 3.50 mmol) was dissolved in a CH3CN (25 ml) at 0° C. Piperidine (21 ml) was added to the solution. After stirring for 30 minutes, the solvent was removed in vacuo to give a residue. Purification by column chromatography (EtOAc eluent) gave the product as a colourless oil (628 mg, 73% yield). 1H NMR (300 MHz, CDCl3), δ: 1.30 (9H, s, (CH3)3), 1.55-1.95 (8H, m, CH2×4), 2.75 (1H, dd, CH, J=7.2, 12.3 Hz), 2.95 (1H, dd, CH, J=4.8, 12.3 Hz), 5.25 (1H, m, CH).

Workup

  1. customthe solvent was removed in vacuo
  2. customto give a residue
  3. customPurification by column chromatography (EtOAc eluent)

Sources & evidence

ORD record
ord-a4f10b583e9b40ccb78fb75605fb8502
Source dataset
uspto-grants-2011_05
Patent number
US07939666B2

Reaction notes

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