Oxygen → HCID 46843534, compound

HRID 1643918Notes

Reaction equation

HRID 1643918 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 50 ml autoclave equipped with a mechanical stirrer was charged with 4.00 g (13.36 mmol) of 6-(3-Fluoro-phenylsulfanyl)-3,4-dihydro-naphthalene-1-carboxylic acid amide, 1.07 mg (0.00134 mmol) of [Ru(OAc)2((S)-MeOBIPHEP)] (S/C 10000) and 28 ml of methanol. The asymmetric hydrogenation was run for 18 h at 40° C. under 9 bar of hydrogen. After cooling to room temperature the pressure was released from the autoclave, the methanol solution was evaporated in vacuo. Isolation as described in example 4 afforded after drying (R)-6-(3-Fluoro-phenylsulfanyl)-1,2,3,4-tetrahydro-naphthalene-1-carboxylic acid amide in quantitative yield as an off-white solid with an enantiomeric ratio of 99:1. The conversion was >=99.8%.

Workup

  1. customthe methanol solution was evaporated in vacuo
  2. customafforded
  3. dry with materialafter drying (R)-6-(3-Fluoro-phenylsulfanyl)-1,2,3,4-tetrahydro-naphthalene-1-carboxylic acid amide in quantitative yield as an off-white solid with an enantiomeric ratio of 99:1

Sources & evidence

ORD record
ord-d891a5e2910642408ae78f7cb5523f40
Source dataset
uspto-grants-2012_02
Patent number
US08119842B2

Reaction notes

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