2-[(2S)-2-[[(2R)-2-(4-Benzyloxyphenyl)-2-hydroxyethyl]-amino]-1,2,3,4-tetrahydronaphthalen-7-yloxy]-N,N-dimethylacetamide → 2-[(2S)-2-[[(2R)-2-hydroxy-2-(4-hydroxyphenyl)ethyl]amino]-1,2,3,4-tetrahydronaphthalen-7-yloxy]-N,N-dimethylacetamide

HRID 1003287Notes

Reaction equation

HRID 1003287 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([OH:35])[CH2:16][NH:17][C@H:18]2[CH2:27][CH2:26][C:25]3[C:20](=[CH:21][C:22]([O:28][CH2:29][C:30]([N:32]([CH3:34])[CH3:33])=[O:31])=[CH:23][CH:24]=3)[CH2:19]2)=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].C(O)C>[OH:35][C@H:15]([C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=1)[CH2:16][NH:17][C@H:18]1[CH2:27][CH2:26][C:25]2[C:20](=[CH:21][C:22]([O:28][CH2:29][C:30]([N:32]([CH3:33])[CH3:34])=[O:31])=[CH:23][CH:24]=2)[CH2:19]1

Participants

4

Reactant 1

HCID 573186072-[(2S)-2-[[(2R)-2-(4-Benzyloxyphenyl)-2-hydroxyethyl]-amino]-1,2,3,4-tetrahydronaphthalen-7-yloxy]-N,N-dimethylacetamide

Product 1

HCID 98214472-[(2S)-2-[[(2R)-2-hydroxy-2-(4-hydroxyphenyl)ethyl]amino]-1,2,3,4-tetrahydronaphthalen-7-yloxy]-N,N-dimethylacetamideYield 90.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-[(2S)-2-[[(2R)-2-(4-Benzyloxyphenyl)-2-hydroxyethyl]-amino]-1,2,3,4-tetrahydronaphthalen-7-yloxy]-N,N-dimethylacetamide (273 mg) and 10% palladium on activated carbon (60 mg) were suspended in ethanol (5.5 ml). After the mixture was stirred at room temperature for 12 hours under hydrogen atmosphere, the catalyst was filtered off and the filtrate was concentrated in vacuo. Recrystallization of the resulting residue from methanol gave 2-[(2S)-2-[[(2R)-2-hydroxy-2-(4-hydroxyphenyl)ethyl]amino]-1,2,3,4-tetrahydronaphthalen-7-yloxy]-N,N-dimethylacetamide (200 mg) having a melting point of 169-172° C.

Workup

  1. filtrationthe catalyst was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customRecrystallization of the resulting residue from methanol

Sources & evidence

ORD record
ord-9c31e155e3f2447fabb1c068d27f5689
Source dataset
uspto-grants-2000_04
Patent number
US06046192

Reaction notes

Loading…