Oxygen → HCID 46843534, compound

HRID 1643915Notes

Reaction equation

HRID 1643915 reaction equation
O=O.[F:3][C:4]1[CH:5]=[C:6]([S:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[C:17]([C:21]([NH2:23])=[O:22])=[CH:16][CH2:15][CH2:14]3)[CH:7]=[CH:8][CH:9]=1.[H][H]>CO>[F:3][C:4]1[CH:5]=[C:6]([S:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[C@H:17]([C:21]([NH2:23])=[O:22])[CH2:16][CH2:15][CH2:14]3)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 977OxygenHCID 59378877HCID 59378877, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 46843534HCID 46843534, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a glove box (O2 content≦2 ppm) a 6 ml autoclave equipped with a glass insert and a magnetic stirring bar was charged with 50 mg (0.167 mmol) of 6-(3-fluoro-phenylsulfanyl)-3,4-dihydro-naphthalene-1-carboxylic acid amide, 6.45 mg (0.00668 mmol) of [Ru(trifluoroacetate)2((S)-pTol-MeOBIPHEP)] (S/C 25) and 1 ml of methanol. The asymmetric hydrogenation was run for 19.5 hours at 40° C. under 40 bar of hydrogen. After cooling to room temperature the pressure was released from the autoclave, the methanol solution was filtered through a silicagel pad and evaporated in vacuo to give (R)-6-(3-fluoro-phenylsulfanyl)-1,2,3,4-tetrahydro-naphthalene-1-carboxylic acid amide in quantitative yield and with an enantiomeric ratio of 99:1. The conversion was >=99.9%.

Workup

  1. filtrationthe methanol solution was filtered through a silicagel pad
  2. customevaporated in vacuo

Sources & evidence

ORD record
ord-93c9ba3451904b11bdbb4a8c53612996
Source dataset
uspto-grants-2012_02
Patent number
US08119842B2

Reaction notes

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