Triphenylphosphine → N-BOC-3-(S)-thioacetoxy-piperidine

HRID 416122Notes

Reaction equation

HRID 416122 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([OH:14])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[S:15]1C=C[CH:17]=[C:16]1CC(O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([O:14][C:16](=[S:15])[CH3:17])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 159702-Thiopheneacetic acidHCID 1514398(R)-1-Boc-3-hydroxypiperidine

Product 1

HCID 86598697N-BOC-3-(S)-thioacetoxy-piperidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2.2 g of N—BOC-3-(R)-hydroxy-piperidine in 10 ml of THF is added under argon and 1 ml of thiolacetic acid to a solution of 3.4 g of triphenylphosphine and 2.65 ml of azadicarbonic acid-isopropylate in 10 ml of THF. The mixture obtained is kept for 18 hours at 70°, solvent is evaporated and the evaporation residue obtained is subjected to chromatography. N—BOC-3-(S)-thioacetoxy-piperidine is obtained. 1H-NMR (CDCl3): 3.78 (dd,1H,NCH2CHS, J=3.1 Hz, J=13.3 Hz), 3.5-3.6 (m,2H, CHSC═O, NCH2CH2), 2.32(s,3H,SC═OCH3),1.46(s,9H, tert.butyl)

Workup

  1. customThe mixture obtained
  2. customsolvent is evaporated
  3. customthe evaporation residue obtained

Sources & evidence

ORD record
ord-ec1f5694e62f48a79004808aa6d811c8
Source dataset
uspto-grants-2012_01
Patent number
US08088823B2

Reaction notes

Loading…