Pyridine → HCID 59122959, compound

HRID 1744833Notes

Reaction equation

HRID 1744833 reaction equation
[N:1]([C@@H:4]1[CH2:8][CH2:7][CH2:6][C@H:5]1[OH:9])=[N+:2]=[N-:3].N1C=CC=CC=1.[N+:16]([C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1)([O-:18])=[O:17].[N+](C1C=CC(S(O)(=O)=O)=CC=1)([O-])=O>C(Cl)Cl>[N:1]([C@@H:4]1[CH2:8][CH2:7][CH2:6][C@H:5]1[O:9][S:25]([C:22]1[CH:21]=[CH:20][C:19]([N+:16]([O-:18])=[O:17])=[CH:24][CH:23]=1)(=[O:26])=[O:27])=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 1049Pyridine2×HCID 74044-Nitrobenzenesulfonyl chlorideHCID 87404-Nitrobenzenesulfonic acidHCID 13737690HCID 13737690, compound

Product 1

HCID 59122959HCID 59122959, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (±)-trans-2-azido-cyclopentanol (1.27 g, 10.0 mmol) (Zhang, Z. da; Scheffold, R. Helv. Chim. Acta 1993, 76, 2602) in CH2Cl2 (14 mL) at 0° C. was treated successively with pyridine (0.88 mL, 10.9 mmol) and 4-nitro-benzenesulfonyl chloride (2.22 g, 10.0 mmol) and allowed to warm to room temperature slowly. The reaction was stirred for 4 d, during which additional pyridine (0.9 mL, 11 mmol) and 4-nitro-benzenesulfonic acid (2.2 g, 10 mmol) was added, and partitioned between CH2Cl2 and 1 N HCl. The aqueous phase was extracted with CH2Cl2 and the extracts were washed with saturated NaHCO3, dried and concentrated. Chromatography of the residue with 10:1–4:1 hexanes:EtOAc gave the product (2.63 g, 84%) as a yellow oil: 1H NMR δ 1.61–1.90 (m, 4H), 2.00–2.16 (m, 2H), 3.96 (m, 1H), 4.72 (m, 1H), 8.14 (m, 2H), 8.43 (m, 2H).

Workup

  1. additionwas added
  2. custompartitioned between CH2Cl2 and 1 N HCl
  3. extractionThe aqueous phase was extracted with CH2Cl2
  4. washthe extracts were washed with saturated NaHCO3
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0620cdf36cf341638a8670ac34e8abac
Source dataset
uspto-grants-2006_03
Patent number
US07019007B2

Reaction notes

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