HCID 24996234, compound → HCID 67020012, compound

HRID 1673243Notes

Reaction equation

HRID 1673243 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:25](=[O:26])[CH2:24][C:23]([CH3:28])([CH3:27])[O:22][C:11]3=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[CH:4][CH:3]=1>CC(O)C.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]3[C@@H:25]([OH:26])[CH2:24][C:23]([CH3:28])([CH3:27])[O:22][C:11]3=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 24996234HCID 24996234, compound

Product 1

HCID 67020012HCID 67020012, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of Example 1 (14.1 g, 32.5 mmol) and the (S,S) catalyst described by Noyori in Angew. Chem. Int. Ed. Engl. 1997, 36, 285 (998 mg, 1.62 mmol) in IPA (20 mL) and CH2Cl2 (10 mL) was stirred at rt. After 16 h, the reaction mixture was concentrated to give the product, which was taken into the next step without further purification: 1H NMR δ 1.43 (s, 3H), 1.56 (s, 3H), 1.96 (dd, J=9.7, 13.4, 1H), 2.06 (d, J=7.3, 1H), 2.28 (dd, J=6.2, 13.5, 1H), 5.00 (m, 1H), 7.03 (d, J=8.5, 2H), 7.18-7.26 (m, 5H), 7.90 (s, 1H).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customto give the product, which
  3. customwas taken into the next step without further purification

Sources & evidence

ORD record
ord-41359c8f5dca4078a67a873576b2250e
Source dataset
uspto-grants-2011_08
Patent number
US07999107B2

Reaction notes

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