Hydrochloric Acid → HCID 46843534, compound

HRID 1643916Notes

Reaction equation

HRID 1643916 reaction equation
O=O.Cl.[F:4][C:5]1[CH:6]=[C:7]([S:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[C:18]([C:22]([NH2:24])=[O:23])=[CH:17][CH2:16][CH2:15]3)[CH:8]=[CH:9][CH:10]=1.[H][H]>CO>[F:4][C:5]1[CH:6]=[C:7]([S:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[C@H:18]([C:22]([NH2:24])=[O:23])[CH2:17][CH2:16][CH2:15]3)[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 977OxygenHCID 59378877HCID 59378877, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 46843534HCID 46843534, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

In a glove box (O2 content≦2 ppm) a catalyst solution was prepared in the glass insert of a 6 ml autoclave by reacting a solution of 6.45 mg (0.00668 mmol) of [Ru(trifluoroacetate)2((S)-pTol-MeOBIPHEP)] (S/C 25) in 0.5 ml of methanol with 0.5 ml of methanol containing 0.020 mmol of HCl and stirring for 2 h at room temperature. After addition of 50 mg (0.167 mmol) of 6-(3-Fluoro-phenylsulfanyl)-3,4-dihydro-naphthalene-1-carboxylic acid amide, the asymmetric hydrogenation was run for 18 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 98.8:1.2. The conversion was >=99.9%.

Workup

  1. temperatureAfter cooling to room temperature the pressure
  2. filtrationthe methanol solution was filtered through a silicagel pad
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-c4fdc51996ce4ab6b14438336ea6347c
Source dataset
uspto-grants-2012_02
Patent number
US08119842B2

Reaction notes

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