Methanol → HCID 69818080, compound

HRID 2417417Notes

Reaction equation

HRID 2417417 reaction equation
C([N:8]([C@@H:19]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[CH:25][CH:24]=1)[CH2:20][OH:21])[CH2:9][C@@H:10]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=1)[OH:11])C1C=CC=CC=1.CO>[Pd].ClC1C=CC=CC=1>[ClH:18].[ClH:18].[NH2:29][C:26]1[CH:25]=[CH:24][C:23]([CH2:22][C@H:19]([NH:8][CH2:9][C@@H:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[OH:11])[CH2:20][OH:21])=[CH:28][CH:27]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 69817648HCID 69817648, compound

Product 1

HCID 69818080HCID 69818080, compoundYield 312%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7964ChlorobenzeneSolvent

Procedure

To a solution of (2S)-2-[N-benzyl-N-[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-3-(4-nitrophenyl)-1-propanol (5.33 g) in a mixed solvent of methanol (50 ml) and chlorobenzene (50 ml) was added 10% palladium on activated carbon (50% wet, 1.00 g) and the mixture was hydrogenated at 1 atm for 2 hours. The catalyst was filtered off and washed with methanol. The filtrate was concentrated in vacuo to give (2S)-3-(4-aminophenyl)-2-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-1-propanol dihydrochloride (4.95 g) as a pale yellow solid.

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with methanol
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-60f4ea3aa4474c7a9bd7c1303f58e078
Source dataset
uspto-grants-2004_11
Patent number
US06826033B2

Reaction notes

Loading…