(3S,4R)-4-(3-chlorophenyl)-3-(4-chlorophenyl)-3,4-dihydro-2H-1,2-thiazin → (3S,4R)-4-(3-chlorophenyl)-3-(4-chlorophenyl)-1,2-thiazinan

HRID 932039Notes

Reaction equation

HRID 932039 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]2[CH:13]=[CH:12][S:11][NH:10][C@@H:9]2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[CH:5]=[CH:6][CH:7]=1>ClCCl.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CC=CCCC=C1.C1C=CN=CC=1.F[P-](F)(F)(F)(F)F.[Ir]>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]2[CH2:13][CH2:12][S:11][NH:10][C@@H:9]2[C:14]2[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 67999141(3S,4R)-4-(3-chlorophenyl)-3-(4-chlorophenyl)-3,4-dihydro-2H-1,2-thiazin

Product 1

HCID 68000201(3S,4R)-4-(3-chlorophenyl)-3-(4-chlorophenyl)-1,2-thiazinan

Reagents, catalysts & solvents 2

HCID 5702647(1,5-Cyclooctadiene)pyridine(tricyclohexylphosphine)iridium hexafluorophosphateCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 4.14 g (11.69 mmol) of (3S,4R)-4-(3-chlorophenyl)-3-(4-chlorophenyl)-3,4-dihydro-2H-1,2-thiazin (Example 117, Step B) in dichloromethane (63.0 mL) was purged with argon three times, and then Crabtree's catalyst (835.2 mg, 1.027 mmol) was added to the reaction mixture. The reaction was purged again with argon, and then a hydrogen atmosphere was placed over the reaction. The solution was stirred at ambient temperature for 15 hours, at which point the reaction was concentrated down to an oil. Purification by flash chromatography on silica gel (0 to 4% MeOH in DCM gradient) provided the title compound as a tan solid.

Workup

  1. customThe reaction was purged again with argon
  2. customa hydrogen atmosphere was placed over the reaction
  3. concentrationwas concentrated down to an oil
  4. customPurification by flash chromatography on silica gel (0 to 4% MeOH in DCM gradient)

Sources & evidence

ORD record
ord-d8611dab00ef46b29bf93e2d003d1f79
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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